ACS Publications. Most Trusted. Most Cited. Most Read
Donor–Acceptor Fluorophores for Visible-Light-Promoted Organic Synthesis: Photoredox/Ni Dual Catalytic C(sp3)–C(sp2) Cross-Coupling

OR SEARCH CITATIONS

My Activity
Publications

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:ACS Catal. 2016, 6, 2, 873-877
    ADDITION/CORRECTION. This article has been corrected. View the notice.
    Letter

    Donor–Acceptor Fluorophores for Visible-Light-Promoted Organic Synthesis: Photoredox/Ni Dual Catalytic C(sp3)–C(sp2) Cross-Coupling
    Click to copy article linkArticle link copied!

    View Author Information
    Department of Chemistry, University of Nebraska−Lincoln, Lincoln, Nebraska 68588, United States
    *E-mail: [email protected]
    Other Access OptionsSupporting Information (1)

    ACS Catalysis

    Cite this: ACS Catal. 2016, 6, 2, 873–877
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acscatal.5b02204
    Published January 12, 2016
    Copyright © 2016 American Chemical Society
    Request reuse permissions

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    We describe carbazolyl dicyanobenzene (CDCB)-based donor–acceptor (D–A) fluorophores as a class of cheap, easily accessible, and efficient metal-free photoredox catalysts for organic synthesis. By changing the number and position of carbazolyl and cyano groups on the center benzene ring, CDCBs with a wide range of photoredox potentials are obtained to effectively drive the energetically demanding C(sp3)–C(sp2) cross-coupling of carboxylic acids and alkyltrifluoroborates with aryl halides via a photoredox/Ni dual catalysis mechanism. This work validates the utility of D–A fluorophores in guiding the rational design of metal-free photoredox catalysts for visible-light-promoted organic synthesis.

    Copyright © 2016 American Chemical Society

    Subjects

    what are subjects

    Keywords

    what are keywords

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    Supporting Information

    Click to copy section linkSection link copied!

    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acscatal.5b02204.

    • Materials, general procedures, synthesis, the cost calculations for D–A fluorophores, physical measurements, spectroscopic characterizations, CV diagrams, NMR spectra, and HPLC measurements (PDF)

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!

    This article is cited by 709 publications.

    1. Yuto Yoshida, Waka Okada, Kazutake Takada, Shuichi Nakamura, Naoki Yasukawa. Photocatalytic Strategy for Decyanative Transformations Enabled by Amine-Ligated Boryl Radical. Organic Letters 2025, Article ASAP.
    2. Pengfei Li, Yanwei Wang, Hanying Zhao, Youai Qiu. Electroreductive Cross-Coupling Reactions: Carboxylation, Deuteration, and Alkylation. Accounts of Chemical Research 2025, 58 (1) , 113-129. https://doi.org/10.1021/acs.accounts.4c00652
    3. John Marques Dos Santos, David Hall, Biju Basumatary, Megan Bryden, Dongyang Chen, Praveen Choudhary, Thomas Comerford, Ettore Crovini, Andrew Danos, Joydip De, Stefan Diesing, Mahni Fatahi, Máire Griffin, Abhishek Kumar Gupta, Hassan Hafeez, Lea Hämmerling, Emily Hanover, Janine Haug, Tabea Heil, Durai Karthik, Shiv Kumar, Oliver Lee, Haoyang Li, Fabien Lucas, Campbell Frank Ross Mackenzie, Aminata Mariko, Tomas Matulaitis, Francis Millward, Yoann Olivier, Quan Qi, Ifor D. W. Samuel, Nidhi Sharma, Changfeng Si, Leander Spierling, Pagidi Sudhakar, Dianming Sun, Eglė Tankelevičiu̅tė, Michele Duarte Tonet, Jingxiang Wang, Tao Wang, Sen Wu, Yan Xu, Le Zhang, Eli Zysman-Colman. The Golden Age of Thermally Activated Delayed Fluorescence Materials: Design and Exploitation. Chemical Reviews 2024, 124 (24) https://doi.org/10.1021/acs.chemrev.3c00755
    4. Rahul Dev Mandal, Dwaipayan Das, Anindita Sarkar, Moumita Saha, Asish R. Das, Akhilesh Mahato, Anup Pramanik. Photoinduced Regioselective Decarbonylative and Decarboxylative C–O Bond Functionalizations: Approach toward Chemoselective Scissions of Isatoic Anhydride and Unraveling the Enroutes through Control Experiments and DFT Studies. The Journal of Organic Chemistry 2024, 89 (24) , 18069-18080. https://doi.org/10.1021/acs.joc.4c01856
    5. Luigi Dolcini, Andrea Solida, Daniele Lavelli, Andrés Mauricio Hidalgo-Núñez, Tommaso Gandini, Matthieu Fornara, Alessandro Colella, Alberto Bossi, Marta Penconi, Daniele Fiorito, Cesare Gennari, Alberto Dal Corso, Luca Pignataro. Bifunctional Photocatalysts Display Proximity-Enhanced Catalytic Activity in Metallaphotoredox C–O Coupling. ACS Catalysis 2024, 14 (24) , 18651-18659. https://doi.org/10.1021/acscatal.4c05893
    6. Du Hu, Haowen Dang, Zhen Liang, Donghao Wang, Yunyun Du, Chao Shen, Jiabin Shen, Min Wang. Visible-Light-Mediated Nucleophilic Addition of Alkene with Aldehyde: Synthesis of Secondary Alcohols. Organic Letters 2024, 26 (50) , 10797-10802. https://doi.org/10.1021/acs.orglett.4c03819
    7. Chen Zhu, Yan-Xiang Li, Chun-Hua Liu, Huai-Ping Cong, Yuan-Yuan Zhu, Wenbin Lin. Integration of N-Aryl Phenoxazine Photosensitizers and Nickel Catalysts in Polymer Supports Enhances Photocatalytic Organic Transformations. ACS Catalysis 2024, 14 (23) , 17609-17621. https://doi.org/10.1021/acscatal.4c04920
    8. Fu Ye, Weiming Yuan. Three-Component Regioselective Aryl- and Alkenyl-Aminoalkylation of Alkenes via Cooperative Photoredox/Nickel Catalysis. The Journal of Organic Chemistry 2024, 89 (23) , 17708-17719. https://doi.org/10.1021/acs.joc.4c02482
    9. Jiawen Zhang, Teng-Fei Xiao, Hongmei Zhao, Jie Kong, Zhuoran Kuang, Meng Zhou, Guo-Qiang Xu, Yang Li, Andong Xia. Photocatalytic Mechanisms of Organic Thermally Activated Delayed Fluorescence Compounds. The Journal of Physical Chemistry Letters 2024, 15 (47) , 11784-11791. https://doi.org/10.1021/acs.jpclett.4c02670
    10. Yue Zhang, Ting Wang, Yuan-Yuan Liu, Zheng-Bing Zhang, Pan Han, Linhai Jing. Organic Photoredox-Catalyzed Hydrosilylation of Vinylboronic Esters for the Synthesis of Geminal and Vicinal Borosilanes. The Journal of Organic Chemistry 2024, 89 (22) , 16463-16472. https://doi.org/10.1021/acs.joc.4c01731
    11. Tao Yang, Wenhui Xiong, Guangyu Sun, Weiran Yang, Mandi Lu, Ming Joo Koh. Multicomponent Construction of Tertiary Alkylamines by Photoredox/Nickel-Catalyzed Aminoalkylation of Organohalides. Journal of the American Chemical Society 2024, 146 (42) , 29177-29188. https://doi.org/10.1021/jacs.4c11602
    12. Yi Liu, Guan-Hua Xue, Zhen He, Jun-Ping Yue, Min Pan, Lei Song, Wei Zhang, Jian-Heng Ye, Da-Gang Yu. Visible-Light Photoredox-Catalyzed Direct Carboxylation of Tertiary C(sp3)–H Bonds with CO2: Facile Synthesis of All-Carbon Quaternary Carboxylic Acids. Journal of the American Chemical Society 2024, 146 (41) , 28350-28359. https://doi.org/10.1021/jacs.4c09558
    13. Chunhua Ma, Qing Guo, Hui Meng, Shengnan Yan, Qingjie Ding, Yuqin Jiang, Bing Yu. Photoredox-Catalyzed Carbamoyl Radical-Initiated Dearomative Spirocyclization To Access Spiro-Cyclohexadiene Oxindoles. Organic Letters 2024, 26 (40) , 8503-8508. https://doi.org/10.1021/acs.orglett.4c03045
    14. Meng Lu, Shuai-Bing Zhang, Run-Han Li, Long-Zhang Dong, Ming-Yi Yang, Pei Huang, Yu-Fei Liu, Ze-Hui Li, Han Zhang, Mi Zhang, Shun-Li Li, Ya-Qian Lan. 3D Covalent Organic Frameworks with 16-Connectivity for Photocatalytic C(sp3)–C(sp2) Cross-Coupling. Journal of the American Chemical Society 2024, 146 (37) , 25832-25840. https://doi.org/10.1021/jacs.4c08951
    15. Tian Wang, Zengyu Zhang, Fan Gao, Xiaoyu Yan. Homologation of Ketones: Direct Transformation of Alkyl Ketones to Aryl Ketones via Photoredox Catalyzed Deacylation-Aroylation Sequence. Organic Letters 2024, 26 (32) , 6915-6920. https://doi.org/10.1021/acs.orglett.4c02576
    16. Qing-Zhu Li, Mei-Hao He, Rong Zeng, Yuan-Yuan Lei, Zhao-Yuan Yu, Min Jiang, Xiang Zhang, Jun-Long Li. Molecular Editing of Ketones through N-Heterocyclic Carbene and Photo Dual Catalysis. Journal of the American Chemical Society 2024, 146 (32) , 22829-22839. https://doi.org/10.1021/jacs.4c08163
    17. Raúl Rojas-Luna, Francisco J. Romero-Salguero, Dolores Esquivel, Souvik Roy. Manipulating the Coordination Structure of Molecular Cobalt Sites in Periodic Mesoporous Organosilica for CO2 Photoreduction. ACS Applied Energy Materials 2024, 7 (14) , 5924-5936. https://doi.org/10.1021/acsaem.4c01161
    18. Rashmi Prakash, Partha Pratim Sen, Vishali Pathania, Sudipta Raha Roy. Photocatalytic Proficiency of Cinnoline Moiety for Cross-Coupling Reactions: A Two in One Photocatalyst. Organic Letters 2024, 26 (28) , 5923-5927. https://doi.org/10.1021/acs.orglett.4c01812
    19. Cai Gao, Yan-Zhi Liu, Yan-Ni Wang, Zhen-Qiang Zhang, Zhuang-Ping Zhan. Regioselective Synthesis of α-Quaternary Amino Acid Derivatives Enabled by Photoinduced Energy Transfer. The Journal of Organic Chemistry 2024, 89 (14) , 10393-10402. https://doi.org/10.1021/acs.joc.4c01153
    20. Xiang-Kui He, Liang-Qiu Lu, Bao-Ru Yuan, Jia-Long Luo, Ying Cheng, Wen-Jing Xiao. Desymmetrization–Addition Reaction of Cyclopropenes to Imines via Synergistic Photoredox and Cobalt Catalysis. Journal of the American Chemical Society 2024, 146 (28) , 18892-18898. https://doi.org/10.1021/jacs.4c07096
    21. Xiaogang Tong, Zugen Wu, Hwee Ting Ang, Yidan Miao, Yixin Lu, Jie Wu. Photocatalytic Reductive Functionalization of Aryl Alkynes via Alkyne Radical Anions. ACS Catalysis 2024, 14 (12) , 9283-9293. https://doi.org/10.1021/acscatal.4c02638
    22. Joseph Bohlke, Cameron Armstrong, Thomas Knauber, María González-Esguevillas, David F. Fernández. Sustainable Solvents in Metallaphotoredox Catalysis. ACS Sustainable Chemistry & Engineering 2024, 12 (24) , 8998-9002. https://doi.org/10.1021/acssuschemeng.4c03003
    23. Fu Ye, Songlin Zheng, Yixin Luo, Xiaotian Qi, Weiming Yuan. Ligand-Controlled Regioreversed 1,2-Aryl-Aminoalkylation of Alkenes Enabled by Photoredox/Nickel Catalysis. ACS Catalysis 2024, 14 (11) , 8505-8517. https://doi.org/10.1021/acscatal.4c01312
    24. Guo-Qin Wang, Yue Zhang, Yuan-Xia Zhou, Dan Yang, Pan Han, Lin-Hai Jing, Kai Tang. Photoredox Synthesis of Silicon-Containing Isoindolin-1-ones and Deuterated Analogues Through Hydrosilylation and Deuterium-silylation. The Journal of Organic Chemistry 2024, 89 (11) , 7899-7912. https://doi.org/10.1021/acs.joc.4c00576
    25. Ting Wang, Lu Chen, Yuan-Yuan Liu, Zheng-Bing Zhang, Pan Han, Lin-Hai Jing. Silylation and (Hetero)aryl/alkenylation of Unactivated Alkenes via Radical-Mediated Distal 1,4-Migration with Hydrosilanes under Organophotocatalysis. Organic Letters 2024, 26 (21) , 4526-4531. https://doi.org/10.1021/acs.orglett.4c01414
    26. Jiashun Zhu, Yu Hong, Yuxin Wang, Yirui Guo, Yuru Zhang, Zhigang Ni, Wanmei Li, Jun Xu. Synthesis of 1-(Halo)alkyl-3-heteroaryl Bicyclo[1.1.1]pentanes Enabled by a Photocatalytic Minisci-type Multicomponent Reaction. ACS Catalysis 2024, 14 (8) , 6247-6258. https://doi.org/10.1021/acscatal.4c00740
    27. Sen Li, Lei Zhou. Photocatalytic (3 + 3) Annnulation of Vinyldiazo Compounds and Aminocyclopropanes. Organic Letters 2024, 26 (15) , 3294-3298. https://doi.org/10.1021/acs.orglett.4c00963
    28. Akira Shiozuka, Di Wu, Kyohei Kawashima, Toshifumi Mori, Kohei Sekine, Yoichiro Kuninobu. Carbamoylarylation of Alkenes with N-Aryl Oxamic Acids Involving 1,4-Aryl Migration Via C(aryl)–N Bond Cleavage. ACS Catalysis 2024, 14 (8) , 5972-5977. https://doi.org/10.1021/acscatal.4c00523
    29. Gang Liu, Haigen Shen, Zhaobin Wang. Access to All-Carbon Quaternary Centers by Photocatalytic Fluoroalkylation of α-Halo Carbonyl Compounds. Organic Letters 2024, 26 (9) , 1863-1867. https://doi.org/10.1021/acs.orglett.4c00041
    30. Hui Zhao, Yingxiao Zong, Yue Sun, Guanghui An, Junke Wang. An Organocatalytic System for Z-Alkene Synthesis via a Hydrogen-Bonding-Assisted Photoinduced Electron Donor–Acceptor Complex. Organic Letters 2024, 26 (8) , 1739-1744. https://doi.org/10.1021/acs.orglett.4c00433
    31. Weichen Wang, Chaoren Shen, Linli Zhang, Kaiwu Dong. Synthesis of Chiral α-Aryl Ketones by Photoredox/Nickel-Catalyzed Enantioconvergent Acyl Cross-Coupling with Organotrifluoroborate. Organic Letters 2024, 26 (4) , 850-854. https://doi.org/10.1021/acs.orglett.3c04004
    32. Chao Sun, Quan Zhou, Chuan-Ying Li, Zhong-Wei Hou, Lei Wang. Photoredox-Catalyzed Defluorinative Carboxylation of gem-Difluorostyrenes with Formate Salt. Organic Letters 2024, 26 (4) , 883-888. https://doi.org/10.1021/acs.orglett.3c04071
    33. Yunfei Guo, Jipeng Qi, Hongyu Guo, Rongfang Liu, Rong Zhou. Cross-Coupling of Benzylic and Aldehydic C–H Bonds via Photocatalytic Tandem Radical–Radical Coupling and Acceptorless Alcohol Dehydrogenation. The Journal of Organic Chemistry 2024, 89 (3) , 2032-2038. https://doi.org/10.1021/acs.joc.3c02427
    34. Yutao Shi, Jinhuan Nie, Zhijie Wu, Xiaochen Ji, Huawen Huang. Photoredox Enabled Defluorinative Benzylation of Trifluoromethyl Alkenes with Alkylarenes. Organic Letters 2024, 26 (1) , 100-105. https://doi.org/10.1021/acs.orglett.3c03713
    35. Congjian Xia, Haiyang Hu, Wengang Xu, Baokai Yang, Qi Shao, Mingbo Wu. Defluoroalkylation of gem-Difluoroalkenes with Alcohols via C–F/C–H Coupling. Organic Letters 2024, 26 (1) , 310-314. https://doi.org/10.1021/acs.orglett.3c03982
    36. Cheng Huang, Peng Xiao, Zhong-Ming Ye, Chen-Lu Wang, Chen Kang, Sheng Tang, Zhenhong Wei, Hu Cai. Direct C(sp3)–H Arylation of Unprotected Benzyl Anilines and Alkylarenes by Organocatalysis under Visible Light. Organic Letters 2024, 26 (1) , 304-309. https://doi.org/10.1021/acs.orglett.3c03980
    37. William Whitaker, Igor V. Sazanovich, Yonghwan Kwon, Woojin Jeon, Min Sang Kwon, Andrew J. Orr-Ewing. Characterization of the Reversible Intersystem Crossing Dynamics of Organic Photocatalysts Using Transient Absorption Spectroscopy and Time-Resolved Fluorescence Spectroscopy. The Journal of Physical Chemistry A 2023, 127 (51) , 10775-10788. https://doi.org/10.1021/acs.jpca.3c04780
    38. Quanyuan Wang, Ya Chen, Keyi Peng, Yue Li, Lilei Cheng, Guo-Jun Deng. Three-Component Cross-Electrophile 1,4-Alkylarylation of 1,3-Enynes by Merging Nickel and Photoredox Catalysis. Organic Letters 2023, 25 (49) , 8889-8894. https://doi.org/10.1021/acs.orglett.3c03677
    39. Siyu Xie, Lin Ma, Teng-Fei Xiao, Jiawen Zhang, Jie Kong, Zhuoran Kuang, Meng Zhou, Guo-Qiang Xu, Yang Li, Andong Xia. Exploring Solvent Polarity-Dependent Photocatalysis Mechanism of Organic Photoredox Catalysts. The Journal of Physical Chemistry B 2023, 127 (45) , 9813-9821. https://doi.org/10.1021/acs.jpcb.3c05879
    40. Wenlong Wang, Xueyuan Yan, Fu Ye, Songlin Zheng, Genping Huang, Weiming Yuan. Nickel/Photoredox Dual-Catalyzed Regiodivergent Aminoalkylation of Unactivated Alkyl Halides. Journal of the American Chemical Society 2023, 145 (42) , 23385-23394. https://doi.org/10.1021/jacs.3c09705
    41. Yasuhiro Yamashita, Yoshihiro Ogasawara, Trisha Banik, Shu̅ Kobayashi. Photoinduced Efficient Catalytic α-Alkylation Reactions of Active Methylene and Methine Compounds with Nonactivated Alkenes. Journal of the American Chemical Society 2023, 145 (42) , 23160-23166. https://doi.org/10.1021/jacs.3c07436
    42. Luigi Dolcini, Tommaso Gandini, Riccardo Castiglioni, Alberto Bossi, Marta Penconi, Alberto Dal Corso, Cesare Gennari, Luca Pignataro. Visible Light-Promoted β-Functionalization of Carbonyl Compounds in the Presence of Organic Dyes. The Journal of Organic Chemistry 2023, 88 (20) , 14283-14291. https://doi.org/10.1021/acs.joc.3c00890
    43. Akira Matsumoto, Natsumi Maeda, Keiji Maruoka. Bidirectional Elongation Strategy Using Ambiphilic Radical Linchpin for Modular Access to 1,4-Dicarbonyls via Sequential Photocatalysis. Journal of the American Chemical Society 2023, 145 (37) , 20344-20354. https://doi.org/10.1021/jacs.3c05337
    44. Junqing Guo, Derek Norris, Antonio Ramirez, Jack L. Sloane, Eric M. Simmons, Jacob M. Ganley, Martins S. Oderinde, T. G. Murali Dhar, Geraint H. M. Davies, Trevor C. Sherwood. Unlocking Tertiary Acids for Metallaphotoredox C(sp2)–C(sp3) Decarboxylative Cross-Couplings. ACS Catalysis 2023, 13 (18) , 11910-11918. https://doi.org/10.1021/acscatal.3c03353
    45. Ryoga Hojo, Katrina Bergmann, Seja A. Elgadi, Don M. Mayder, Megan A. Emmanuel, Martins S. Oderinde, Zachary M. Hudson. Imidazophenothiazine-Based Thermally Activated Delayed Fluorescence Materials with Ultra-Long-Lived Excited States for Energy Transfer Photocatalysis. Journal of the American Chemical Society 2023, 145 (33) , 18366-18381. https://doi.org/10.1021/jacs.3c04132
    46. Xiaona Yang, Yunfei Guo, Hong’en Tong, Hongyu Guo, Rongfang Liu, Rong Zhou. Photochemical Hydrogen Atom Transfer Catalysis for Dehydrogenation of Alcohols To Form Carbonyls. Organic Letters 2023, 25 (29) , 5486-5491. https://doi.org/10.1021/acs.orglett.3c01917
    47. Dingding Xia, Rongkai Wu, Jinxin Wang, Xinyu Han, Yanchuan Li, Qiannan Li, Xin Luan, Xin Hong, Yu Zhang, Wei-Dong Zhang. Visible-Light-Mediated Energy Transfer Enables Cyclopropanes Bearing Contiguous All-Carbon Quaternary Centers. ACS Catalysis 2023, 13 (14) , 9806-9816. https://doi.org/10.1021/acscatal.3c02350
    48. Mahima Sneha, Georgia L. Thornton, Luke Lewis-Borrell, Alison S. H. Ryder, Samuel G. Espley, Ian P. Clark, Alexander J. Cresswell, Matthew N. Grayson, Andrew J. Orr-Ewing. Photoredox-HAT Catalysis for Primary Amine α-C–H Alkylation: Mechanistic Insight with Transient Absorption Spectroscopy. ACS Catalysis 2023, 13 (12) , 8004-8013. https://doi.org/10.1021/acscatal.3c01474
    49. Jaume Rostoll-Berenguer, Víctor García-García, Gonzalo Blay, José R. Pedro, Carlos Vila. Organophotoredox 1,6-Addition of 3,4-Dihydroquinoxalin-2-ones to para-Quinone Methides Using Visible Light. ACS Organic & Inorganic Au 2023, 3 (3) , 130-135. https://doi.org/10.1021/acsorginorgau.2c00064
    50. Xiaoli He, Jiahao Ling, Zhixing Fang, Lei Zhou. Synthesis of 2-Fluorobenzofuran by Photocatalytic Defluorinative Coupling and 5-endo-trig Cyclization. The Journal of Organic Chemistry 2023, 88 (11) , 7586-7591. https://doi.org/10.1021/acs.joc.3c00559
    51. Sangil Han, Kyra L. Samony, Rifat N. Nabi, Campbell A. Bache, Daniel K. Kim. Hydrotrifluoroacetylation of Alkenes via Designer Masked Acyl Reagents. Journal of the American Chemical Society 2023, 145 (21) , 11530-11536. https://doi.org/10.1021/jacs.3c04294
    52. Wei Li, Jie Qiu, Hengyuan Li, Wanli Chen, Cheng Hou, Huaifeng Li. Indolization of N-Aryl Tertiary Amines with Diazoacetates by a Single Organophotocatalyst. Organic Letters 2023, 25 (20) , 3778-3783. https://doi.org/10.1021/acs.orglett.3c01288
    53. Alessa B. Rolka, Nataliya Archipowa, Roger J. Kutta, Burkhard König, F. Dean Toste. Hybrid Catalysts for Enantioselective Photo-Phosphoric Acid Catalysis. The Journal of Organic Chemistry 2023, 88 (10) , 6509-6522. https://doi.org/10.1021/acs.joc.3c00191
    54. Megan Amy Bryden, Francis Millward, Tomas Matulaitis, Dongyang Chen, Marco Villa, Andrea Fermi, Sultan Cetin, Paola Ceroni, Eli Zysman-Colman. Moving Beyond Cyanoarene Thermally Activated Delayed Fluorescence Compounds as Photocatalysts: An Assessment of the Performance of a Pyrimidyl Sulfone Photocatalyst in Comparison to 4CzIPN. The Journal of Organic Chemistry 2023, 88 (10) , 6364-6373. https://doi.org/10.1021/acs.joc.2c01137
    55. Pedro H. R. Oliveira, Éverton A. Tordato, Jeimy A. C. Vélez, Pablo S. Carneiro, Márcio W. Paixão. Visible-Light Mediated Carbamoylation of Nitrones under a Continuous Flow Regime. The Journal of Organic Chemistry 2023, 88 (10) , 6407-6419. https://doi.org/10.1021/acs.joc.2c02266
    56. Emanuele Pinosa, Elena Bassan, Sultan Cetin, Marco Villa, Simone Potenti, Francesco Calogero, Andrea Gualandi, Andrea Fermi, Paola Ceroni, Pier Giorgio Cozzi. Light-Induced Access to Carbazole-1,3-dicarbonitrile: A Thermally Activated Delayed Fluorescent (TADF) Photocatalyst for Cobalt-Mediated Allylations. The Journal of Organic Chemistry 2023, 88 (10) , 6390-6400. https://doi.org/10.1021/acs.joc.2c01825
    57. Seoksun Kim, Beomsoon Park, Geun Seok Lee, Soon Hyeok Hong. Synthesis of α-Aminoacetals via Decarboxylative Coupling of Imine and 2,2,-Diethoxyacetic Acid. The Journal of Organic Chemistry 2023, 88 (10) , 6532-6537. https://doi.org/10.1021/acs.joc.2c01941
    58. Peizhuo Lv, Ali Wang, Xin Xie, Yulong Chen, Yuanhong Liu. Photoredox/Nickel Dual-Catalyzed Regioselective Allylic Arylations of Allyl Trifluoroborates with Aryl Halides. Organic Letters 2023, 25 (18) , 3319-3324. https://doi.org/10.1021/acs.orglett.3c01147
    59. Cai Gao, Jiahao Zeng, Xianming Zhang, Yanzhi Liu, Zhuang-ping Zhan. A Photosensitizer for N–O Bond Activation: 2,7-Br-4CzIPN-Catalyzed Difunctionalization of Alkenes with Oxime Esters. Organic Letters 2023, 25 (17) , 3146-3151. https://doi.org/10.1021/acs.orglett.3c01073
    60. Xinhan Li, Hengyuan Zhao, Li Meng, Jun Dong, Chunhui Yang, Zixiang Wei, Xianming Wang, Jianbin Xu, Baomin Fan. Divergent Radical Cyclization and Hydroaminoalkylation of N-Arylacrylamides Using Photoredox Catalysis. The Journal of Organic Chemistry 2023, 88 (9) , 5300-5310. https://doi.org/10.1021/acs.joc.2c02709
    61. Paolo Piacentini, James M. Fordham, Eloisa Serrano, Luca Hepp, Marco Santagostino. Temperature-Controlled Photoreactors and ChemBeads as Key Technologies for Robust and Practical Photochemical HTE. Organic Process Research & Development 2023, 27 (4) , 798-810. https://doi.org/10.1021/acs.oprd.3c00061
    62. Wei Xiong, Xuan Jiang, Wen-Cheng Wang, Ying Cheng, Liang-Qiu Lu, Ke Gao, Wen-Jing Xiao. Dynamic Kinetic Reductive Conjugate Addition for Construction of Axial Chirality Enabled by Synergistic Photoredox/Cobalt Catalysis. Journal of the American Chemical Society 2023, 145 (14) , 7983-7991. https://doi.org/10.1021/jacs.2c13538
    63. Hao Jiang, Xiang-Kui He, Xuan Jiang, Wei Zhao, Liang-Qiu Lu, Ying Cheng, Wen-Jing Xiao. Photoinduced Cobalt-Catalyzed Desymmetrization of Dialdehydes to Access Axial Chirality. Journal of the American Chemical Society 2023, 145 (12) , 6944-6952. https://doi.org/10.1021/jacs.3c00462
    64. Yumo Zhao, Yi Wan, Qiyang Yuan, Jinlian Wei, Yongqiang Zhang. Photocatalytic C–Si Bond Formations Using Pentacoordinate Silylsilicates as Silyl Radical Precursors: Synthetic Tricks Using Old Reagents. Organic Letters 2023, 25 (9) , 1386-1391. https://doi.org/10.1021/acs.orglett.3c00096
    65. Ning Xian, Jiang Yin, Xiaochen Ji, Guo-Jun Deng, Huawen Huang. Visible-Light-Mediated Photoredox Carbon Radical Formation from Aqueous Sulfoxonium Ylides. Organic Letters 2023, 25 (7) , 1161-1165. https://doi.org/10.1021/acs.orglett.3c00143
    66. Anjan Das, Anthony Choi, Iain Coldham. Photocatalysis and Kinetic Resolution by Lithiation to Give Enantioenriched 2-Arylpiperazines. Organic Letters 2023, 25 (6) , 987-991. https://doi.org/10.1021/acs.orglett.3c00074
    67. Zi-Gang Ren, Wan-Lei Yu, Hai-Xue Zheng, Peng-Fei Xu. PCET-Mediated Ring-Opening Alkenylation of Cycloalkanols via Dual Photoredox and Cobalt Catalysis. Organic Letters 2023, 25 (1) , 93-98. https://doi.org/10.1021/acs.orglett.2c03894
    68. Samrat Kundu, Lisa Roy, Modhu Sudan Maji. Development of Carbazole-Cored Organo-Photocatalyst for Visible Light-Driven Reductive Pinacol/Imino-Pinacol Coupling. Organic Letters 2022, 24 (49) , 9001-9006. https://doi.org/10.1021/acs.orglett.2c03600
    69. Narenderreddy Katta, Quan-Qing Zhao, Tirtha Mandal, Oliver Reiser. Divergent and Synergistic Photocatalysis: Hydro- and Oxoalkylation of Vinyl Arenes for the Stereoselective Synthesis of Cyclopentanols via a Formal [4+1]-Annulation of 1,3-Dicarbonyls. ACS Catalysis 2022, 12 (22) , 14398-14407. https://doi.org/10.1021/acscatal.2c04736
    70. Carla Casadevall Jordi Aragón Santiago Cañellas Miquel A. Pericàs Julio Lloret-Fillol Xisco Caldentey . Development of Advanced High Throughput Experimentation Platforms for Photocatalytic Reactions. , 145-165. https://doi.org/10.1021/bk-2022-1419.ch009
    71. Fan-Lin Zeng, Zhi-Yang Zhang, Peng-Cheng Yin, Fu-Kun Cheng, Xiao-Lan Chen, Ling-Bo Qu, Zhong-Yan Cao, Bing Yu. Visible-Light-Induced Cascade Cyclization of 3-(2-(Ethynyl)phenyl)quinazolinones to Phosphorylated Quinolino[2,1-b]quinazolinones. Organic Letters 2022, 24 (43) , 7912-7917. https://doi.org/10.1021/acs.orglett.2c02930
    72. Songlin Zheng, Wenlong Wang, Weiming Yuan. Remote and Proximal Hydroaminoalkylation of Alkenes Enabled by Photoredox/Nickel Dual Catalysis. Journal of the American Chemical Society 2022, 144 (39) , 17776-17782. https://doi.org/10.1021/jacs.2c08039
    73. Wencheng Han, Junqi Su, Jia-Nan Mo, Jiannan Zhao. Photoredox Catalytic Phosphine-Mediated Deoxygenation of Hydroxylamines Enables the Construction of N-Acyliminophosphoranes. Organic Letters 2022, 24 (34) , 6247-6251. https://doi.org/10.1021/acs.orglett.2c02226
    74. Yukang Wang, Liubo Li, Niankai Fu. Electrophotochemical Decarboxylative Azidation of Aliphatic Carboxylic Acids. ACS Catalysis 2022, 12 (17) , 10661-10667. https://doi.org/10.1021/acscatal.2c02934
    75. Julia Soika, Calum McLaughlin, Tomáš Neveselý, Constantin G. Daniliuc, John. J. Molloy, Ryan Gilmour. Organophotocatalytic N–O Bond Cleavage of Weinreb Amides: Mechanism-Guided Evolution of a PET to ConPET Platform. ACS Catalysis 2022, 12 (16) , 10047-10056. https://doi.org/10.1021/acscatal.2c02991
    76. Jonathan D. Ellefsen, Scott J. Miller. Photocatalytic Reductive Olefin Hydrodifluoroalkylation Enabled by Tertiary Amine Reductants Compatible with Complex Systems. The Journal of Organic Chemistry 2022, 87 (15) , 10250-10255. https://doi.org/10.1021/acs.joc.2c01231
    77. Binsong Mu, Le Zhang, Guanghui Lv, Kang Chen, Ting Wang, Jian Chen, Tianle Huang, Li Guo, Zhongzhen Yang, Yong Wu. Access to Phosphine-Containing Quinazolinones Enabled by Photo-Induced Radical Phosphorylation/Cyclization of Unactivated Alkenes. The Journal of Organic Chemistry 2022, 87 (15) , 10146-10157. https://doi.org/10.1021/acs.joc.2c01092
    78. Ewelina Kowalska, Angelika Artelska, Anna Albrecht. Visible Light-Driven Reductive Azaarylation of Coumarin-3-carboxylic Acids. The Journal of Organic Chemistry 2022, 87 (15) , 9645-9653. https://doi.org/10.1021/acs.joc.2c00683
    79. Ryoga Hojo, Alexander M. Polgar, Zachary M. Hudson. Thermally Activated Delayed Fluorescence Sensitizers As Organic and Green Alternatives in Energy-Transfer Photocatalysis. ACS Sustainable Chemistry & Engineering 2022, 10 (30) , 9665-9678. https://doi.org/10.1021/acssuschemeng.2c01426
    80. Jaume Rostoll-Berenguer, María Martín-López, Gonzalo Blay, José R. Pedro, Carlos Vila. Radical Addition of Dihydroquinoxalin-2-ones to Trifluoromethyl Ketones under Visible-Light Photoredox Catalysis. The Journal of Organic Chemistry 2022, 87 (14) , 9343-9356. https://doi.org/10.1021/acs.joc.2c01139
    81. Qing Wang, Ling Yue, Yanyang Bao, Yanan Wang, Danni Kang, Yan Gao, Zheliang Yuan. Oxalates as Activating Groups for Tertiary Alcohols in Photoredox-Catalyzed gem-Difluoroallylation To Construct All-Carbon Quaternary Centers. The Journal of Organic Chemistry 2022, 87 (12) , 8237-8247. https://doi.org/10.1021/acs.joc.2c00664
    82. Cong Luo, Yang Zhou, Hang Chen, Ting Wang, Zheng-Bing Zhang, Pan Han, Lin-Hai Jing. Photoredox Metal-Free Allylic Defluorinative Silylation of α-Trifluoromethylstyrenes with Hydrosilanes. Organic Letters 2022, 24 (23) , 4286-4291. https://doi.org/10.1021/acs.orglett.2c01690
    83. Yuka Tajimi, Yasuhiro Nachi, Ryoko Inada, Ryoga Hashimoto, Mugen Yamawaki, Kei Ohkubo, Toshio Morita, Yasuharu Yoshimi. 9-Cyano-10-methoxycarbonylanthracene as a Visible Organic Photoredox Catalyst in the Two-Molecule Photoredox System. The Journal of Organic Chemistry 2022, 87 (11) , 7405-7413. https://doi.org/10.1021/acs.joc.2c00643
    84. Xuan Jiang, Hao Jiang, Qian Yang, Ying Cheng, Liang-Qiu Lu, Jon A. Tunge, Wen-Jing Xiao. Photoassisted Cobalt-Catalyzed Asymmetric Reductive Grignard-Type Addition of Aryl Iodides. Journal of the American Chemical Society 2022, 144 (18) , 8347-8354. https://doi.org/10.1021/jacs.2c02481
    85. Weidi Zeng, Weiyu Li, Haoguo Chen, Lei Zhou. Relay Photocatalytic Reaction of N-Aryl Amino Acids and 2-Bromo-3,3,3-trifluoropropene: Synthesis of 4-(Difluoromethylidene)-tetrahydroquinolines. Organic Letters 2022, 24 (17) , 3265-3269. https://doi.org/10.1021/acs.orglett.2c01117
    86. Biao Wang, Min-Jie Zhou, Qi-Lin Zhou. Visible-Light-Induced α,γ-C(sp3)–H Difunctionalization of Piperidines. Organic Letters 2022, 24 (15) , 2894-2898. https://doi.org/10.1021/acs.orglett.2c00831
    87. Zhiying Li, Qianjin Lian, Youwei Xu, Yichuan Zhang, Pengfei Zhang, Jin Geng. Aggregation-Induced Emission Luminogen Catalyzed Photocontrolled Reversible Addition–Fragmentation Chain Transfer Polymerization in an Aqueous Environment. Macromolecules 2022, 55 (7) , 2904-2910. https://doi.org/10.1021/acs.macromol.2c00171
    88. Dong Liang, Jia-Rong Chen, Li-Ping Tan, Zi-Wei He, Wen-Jing Xiao. Catalytic Asymmetric Construction of Axially and Centrally Chiral Heterobiaryls by Minisci Reaction. Journal of the American Chemical Society 2022, 144 (13) , 6040-6049. https://doi.org/10.1021/jacs.2c01116
    89. Haifeng Yang, Zheng Huang, Dan Lehnherr, Yu-hong Lam, Sumei Ren, Neil A. Strotman. Efficient Aliphatic Hydrogen-Isotope Exchange with Tritium Gas through the Merger of Photoredox and Hydrogenation Catalysts. Journal of the American Chemical Society 2022, 144 (11) , 5010-5022. https://doi.org/10.1021/jacs.1c13265
    90. Xiaochen Ji, Zhonglin Yang, Xinzhuang Wu, Guo-Jun Deng, Huawen Huang. Photoredox Neutral Decarboxylative Hydroxyalkylations of Heteroarenes with α-Keto Acids. The Journal of Organic Chemistry 2022, 87 (6) , 4168-4182. https://doi.org/10.1021/acs.joc.1c03007
    91. Abdoul G. Diallo, Déborah Paris, Djiby Faye, Sylvain Gaillard, Mark Lautens, Jean-Luc Renaud. Dual Ni/Organophotoredox Catalyzed Allylative Ring Opening Reaction of Oxabenzonorbornadienes and Analogs. ACS Catalysis 2022, 12 (6) , 3681-3688. https://doi.org/10.1021/acscatal.2c00512
    92. Shuai Zhong, Zhiwei Zhou, Feng Zhao, Guojiang Mao, Guo-Jun Deng, Huawen Huang. Deoxygenative C–S Bond Coupling with Sulfinates via Nickel/Photoredox Dual Catalysis. Organic Letters 2022, 24 (9) , 1865-1870. https://doi.org/10.1021/acs.orglett.2c00478
    93. Zhengning Fan, Shenhao Chen, Song Zou, Chanjuan Xi. Direct C–C Bond Formation of Allylic Alcohols with CO2 toward Carboxylic Acids by Photoredox/Nickel Dual Catalysis. ACS Catalysis 2022, 12 (5) , 2781-2787. https://doi.org/10.1021/acscatal.2c00418
    94. Fabio Juliá, Timothée Constantin, Daniele Leonori. Applications of Halogen-Atom Transfer (XAT) for the Generation of Carbon Radicals in Synthetic Photochemistry and Photocatalysis. Chemical Reviews 2022, 122 (2) , 2292-2352. https://doi.org/10.1021/acs.chemrev.1c00558
    95. Philip R. D. Murray, James H. Cox, Nicholas D. Chiappini, Casey B. Roos, Elizabeth A. McLoughlin, Benjamin G. Hejna, Suong T. Nguyen, Hunter H. Ripberger, Jacob M. Ganley, Elaine Tsui, Nick Y. Shin, Brian Koronkiewicz, Guanqi Qiu, Robert R. Knowles. Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis. Chemical Reviews 2022, 122 (2) , 2017-2291. https://doi.org/10.1021/acs.chemrev.1c00374
    96. Daniel A. Corbin, Garret M. Miyake. Photoinduced Organocatalyzed Atom Transfer Radical Polymerization (O-ATRP): Precision Polymer Synthesis Using Organic Photoredox Catalysis. Chemical Reviews 2022, 122 (2) , 1830-1874. https://doi.org/10.1021/acs.chemrev.1c00603
    97. Kitae Kwon, R. Thomas Simons, Meganathan Nandakumar, Jennifer L. Roizen. Strategies to Generate Nitrogen-centered Radicals That May Rely on Photoredox Catalysis: Development in Reaction Methodology and Applications in Organic Synthesis. Chemical Reviews 2022, 122 (2) , 2353-2428. https://doi.org/10.1021/acs.chemrev.1c00444
    98. Ibuki Tanaka, Masaya Sawamura, Yohei Shimizu. Visible Light-Induced Reductive Alkynylation of Aldehydes by Umpolung Approach. Organic Letters 2022, 24 (2) , 520-524. https://doi.org/10.1021/acs.orglett.1c03927
    99. Pete Delgado, Raoul J. Glass, Gina Geraci, Rohit Duvadie, Dyuti Majumdar, Richard I. Robinson, Imran Elmaarouf, Malte Mikus, Kian L. Tan. Use of Green Solvents in Metallaphotoredox Cross-Electrophile Coupling Reactions Utilizing a Lipophilic Modified Dual Ir/Ni Catalyst System. The Journal of Organic Chemistry 2021, 86 (23) , 17428-17436. https://doi.org/10.1021/acs.joc.1c02013
    100. Min He, Xiaoqiang Yu, Yi Wang, Ming Bao. Tunable Redox Potential Photocatalyst: Aggregates of 2,3-Dicyanopyrazino Phenanthrene Derivatives for the Visible-Light-Induced α-Allylation of Amines. The Journal of Organic Chemistry 2021, 86 (21) , 14720-14731. https://doi.org/10.1021/acs.joc.1c01533
    Load more citations
    Download PDF
    Go to ACS Catalysis
    Get e-Alerts
    Get e-Alerts

    ACS Catalysis

    Cite this: ACS Catal. 2016, 6, 2, 873–877
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acscatal.5b02204
    Published January 12, 2016
    Copyright © 2016 American Chemical Society
    Request reuse permissions

    Article Views

    35k

    Altmetric

    -

    Citations

    709
    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.