Photocatalytic Hydrogen-Evolution Cross-Couplings: Benzene C–H Amination and HydroxylationClick to copy article linkArticle link copied!
Abstract
We present a blueprint for aromatic C–H functionalization via a combination of photocatalysis and cobalt catalysis and describe the utility of this strategy for benzene amination and hydroxylation. Without any sacrificial oxidant, we could use the dual catalyst system to produce aniline directly from benzene and ammonia, and phenol from benzene and water, both with evolution of hydrogen gas under unusually mild conditions in excellent yields and selectivities.
Cited By
This article is cited by 298 publications.
- Chen-Yan Cai, Si-Jie Chen, Rohan R. Merchant, Yuzuru Kanda, Tian Qin. C3 Selective Hydroxylation of Pyridines via Photochemical Valence Isomerization of Pyridine N-Oxides. Journal of the American Chemical Society 2024, 146
(35)
, 24257-24264. https://doi.org/10.1021/jacs.4c10057
- Chen-Hong Wang, Jia-Dong Guo, Ji-Xin Yu, Jia Qiao, Bin Chen, Chen-Ho Tung, Li-Zhu Wu. Photocatalytic Cross-Coupling of Aldehydes and Alkenes for Aryl Vinyl Ketones by a Single Catalyst. Organic Letters 2024, 26
(32)
, 6927-6932. https://doi.org/10.1021/acs.orglett.4c02570
- Matthew C. Carson, Cindy R. Liu, Yaning Liu, Marisa C. Kozlowski. Amination of Phenols and Halophenols via Pyridinium–Iridium Dual Photocatalysis. ACS Catalysis 2024, 14
(16)
, 12173-12180. https://doi.org/10.1021/acscatal.4c02797
- Matthew R. Lasky, En-Chih Liu, Matthew S. Remy, Melanie S. Sanford. Visible-Light Photocatalytic C–H Amination of Arenes Utilizing Acridine–Lewis Acid Complexes. Journal of the American Chemical Society 2024, 146
(21)
, 14799-14806. https://doi.org/10.1021/jacs.4c02991
- Shi Ru, Cong-Cong Zhao, Zhikang Wu, Li-Kai Yan, Dejin Zang, Yongge Wei. Molecular Photocatalysts Based on Quinolinium-Grafted Polyoxometalates for Efficient One-Step Aerobic Oxidation of Benzyl Alcohols to Benzoic Acids. ACS Sustainable Chemistry & Engineering 2024, 12
(18)
, 6827-6839. https://doi.org/10.1021/acssuschemeng.3c05573
- Yishou Wang, Ruijie Mi, Songjie Yu, Xingwei Li. Expedient Synthesis of Axially and Centrally Chiral Diaryl Ethers via Cobalt-Catalyzed Photoreductive Desymmetrization. ACS Catalysis 2024, 14
(7)
, 4638-4647. https://doi.org/10.1021/acscatal.4c00001
- Chen Jin, Cailin Ning, Yating Sui, Bingxin Zhang, Xinxin Li, Ling Pan, Qun Liu, Yifei Li. Photoredox-Catalyzed Alkene Amination: C(sp2)–H/N–H Radical–Radical Cross Dehydrogenative Coupling. Organic Letters 2024, 26
(11)
, 2326-2331. https://doi.org/10.1021/acs.orglett.4c00682
- Yongtao Wang, Jiaxin Liu, Wenjing Sun, Yujia Zhou, Xinyu Wang, Qixuan Hu, Zeyu Wen, Jia Yao, Haoran Li. Oxygenation of Phenols with Water as the Oxygen Source and Oxoammonium Salt as the Oxidant. The Journal of Organic Chemistry 2024, 89
(4)
, 2440-2447. https://doi.org/10.1021/acs.joc.3c02448
- Jun-Li Li, Hao-Yuan Li, Shan-Shan Zhang, Shigang Shen, Xiu-Long Yang, Xiaoying Niu. Photoredox/Cobalt-Catalyzed Cascade Oxidative Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles under Oxidant-Free Conditions. The Journal of Organic Chemistry 2023, 88
(21)
, 14874-14886. https://doi.org/10.1021/acs.joc.3c01078
- Wei-Hao Rao, Ying-Ge Li, Li-Li Jiang, Qi Li, Guo-Dong Zou, Xinhua Cao. Metal-Free Selective Ortho-C–H Amidation of Hypervalent(III) Iodobezenes with N-Methoxy Amides under Mild Conditions. The Journal of Organic Chemistry 2023, 88
(19)
, 13825-13837. https://doi.org/10.1021/acs.joc.3c01472
- Hui Li, Takafumi Yatabe, Satoshi Takayama, Kazuya Yamaguchi. Heterogeneously Catalyzed Selective Acceptorless Dehydrogenative Aromatization to Primary Anilines from Ammonia via Concerted Catalysis and Adsorption Control. JACS Au 2023, 3
(5)
, 1376-1384. https://doi.org/10.1021/jacsau.3c00049
- Partha Pratim Sen, Sudipta Raha Roy. Introducing Phenalenyl-Based Organic Lewis Acid as a Photocatalyst to Facilitate Oxidative Azolation of Unactivated Arenes. Organic Letters 2023, 25
(11)
, 1895-1900. https://doi.org/10.1021/acs.orglett.3c00409
- Chang-Ming You, Cheng Huang, Sheng Tang, Peng Xiao, Shengchun Wang, Zhenhong Wei, Aiwen Lei, Hu Cai. N-Allylation of Azoles with Hydrogen Evolution Enabled by Visible-Light Photocatalysis. Organic Letters 2023, 25
(10)
, 1722-1726. https://doi.org/10.1021/acs.orglett.3c00399
- 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
- Jun-Li Li, Xiu-Long Yang, Shigang Shen, Xiaoying Niu. Synthesis of 10-Phenanthrenols via Photosensitized Triplet Energy Transfer, Photoinduced Electron Transfer, and Cobalt Catalysis. The Journal of Organic Chemistry 2022, 87
(24)
, 16458-16472. https://doi.org/10.1021/acs.joc.2c02182
- Pufan Ni, Lei Yang, Yi Shen, Lei Zhang, Yueyue Ma, Maolin Sun, Ruihua Cheng, Jinxing Ye. Synthesis of Phenols from Aryl Ammonium Salts under Mild Conditions. The Journal of Organic Chemistry 2022, 87
(19)
, 12677-12687. https://doi.org/10.1021/acs.joc.2c01133
- Zhen Li, Han Seul Park, Jennifer X. Qiao, Kap-Sun Yeung, Jin-Quan Yu. Ligand-Enabled C–H Hydroxylation with Aqueous H2O2 at Room Temperature. Journal of the American Chemical Society 2022, 144
(39)
, 18109-18116. https://doi.org/10.1021/jacs.2c08332
- Shu-Lin Meng, Chen Ye, Xu-Bing Li, Chen-Ho Tung, Li-Zhu Wu. Photochemistry Journey to Multielectron and Multiproton Chemical Transformation. Journal of the American Chemical Society 2022, 144
(36)
, 16219-16231. https://doi.org/10.1021/jacs.2c02341
- Ritu, Saikat Das, Ya-Ming Tian, Tobias Karl, Nidhi Jain, Burkhard König. Photocatalyzed Dehydrogenation of Aliphatic N-Heterocycles Releasing Dihydrogen. ACS Catalysis 2022, 12
(16)
, 10326-10332. https://doi.org/10.1021/acscatal.2c02830
- Qi-Chao Gan, Zi-Qi Song, Chen-Ho Tung, Li-Zhu Wu. Direct C(sp)–H/Si–H Cross-Coupling via Copper Salts Photocatalysis. Organic Letters 2022, 24
(28)
, 5192-5196. https://doi.org/10.1021/acs.orglett.2c02022
- He Huang, Keri A. Steiniger, Tristan H. Lambert. Electrophotocatalysis: Combining Light and Electricity to Catalyze Reactions. Journal of the American Chemical Society 2022, 144
(28)
, 12567-12583. https://doi.org/10.1021/jacs.2c01914
- Xiaoying Liu, Weikun Chen, Jinglin Zou, Linmin Ye, Youzhu Yuan. Liquid-Phase Amination of Phenol to Aniline over the Pd/MgO Catalyst without External Hydrogen Addition. ACS Sustainable Chemistry & Engineering 2022, 10
(21)
, 6988-6998. https://doi.org/10.1021/acssuschemeng.2c00273
- Soumya Kumar Sinha, Srimanta Guin, Sudip Maiti, Jyoti Prasad Biswas, Sandip Porey, Debabrata Maiti. Toolbox for Distal C–H Bond Functionalizations in Organic Molecules. Chemical Reviews 2022, 122
(6)
, 5682-5841. https://doi.org/10.1021/acs.chemrev.1c00220
- Haifeng Yu, Zheyu Zhang, Xue Zhang, Yupeng Xu, Dongyue Huo, Lanyun Zhang, Wenju Wang. Green Tandem [5C + 1C] Cycloaromatization of α-Alkenoyl Ketene Dithioacetals and Nitroethane in Water: Eco-Friendly Synthesis of Ortho-Acylphenols. The Journal of Organic Chemistry 2022, 87
(5)
, 2985-2996. https://doi.org/10.1021/acs.joc.1c02825
- Long-Long Su, Yi-Wen Zheng, Wen-Guang Wang, Bin Chen, Xiang-Zhu Wei, Li-Zhu Wu, Chen-Ho Tung. Photocatalytic Synthesis of Quinolines via Povarov Reaction under Oxidant-Free Conditions. Organic Letters 2022, 24
(5)
, 1180-1185. https://doi.org/10.1021/acs.orglett.1c04287
- Natalie Holmberg-Douglas, David A. Nicewicz. Photoredox-Catalyzed C–H Functionalization Reactions. Chemical Reviews 2022, 122
(2)
, 1925-2016. https://doi.org/10.1021/acs.chemrev.1c00311
- Amy Y. Chan, Ian B. Perry, Noah B. Bissonnette, Benito F. Buksh, Grant A. Edwards, Lucas I. Frye, Olivia L. Garry, Marissa N. Lavagnino, Beryl X. Li, Yufan Liang, Edna Mao, Agustin Millet, James V. Oakley, Nicholas L. Reed, Holt A. Sakai, Ciaran P. Seath, David W. C. MacMillan. Metallaphotoredox: The Merger of Photoredox and Transition Metal Catalysis. Chemical Reviews 2022, 122
(2)
, 1485-1542. https://doi.org/10.1021/acs.chemrev.1c00383
- Min-Jie Zhou, Lei Zhang, Guixia Liu, Chen Xu, Zheng Huang. Site-Selective Acceptorless Dehydrogenation of Aliphatics Enabled by Organophotoredox/Cobalt Dual Catalysis. Journal of the American Chemical Society 2021, 143
(40)
, 16470-16485. https://doi.org/10.1021/jacs.1c05479
- Enrico Bergamaschi, Christopher Weike, Victor J. Mayerhofer, Ignacio Funes-Ardoiz, Christopher J. Teskey. Dual Photoredox/Cobaloxime Catalysis for Cross-Dehydrogenative α-Heteroarylation of Amines. Organic Letters 2021, 23
(14)
, 5378-5382. https://doi.org/10.1021/acs.orglett.1c01703
- Yan-Lin Li, Shi-Qi Zhang, Jie Chen, Ji-Bao Xia. Highly Regio- and Enantioselective Reductive Coupling of Alkynes and Aldehydes via Photoredox Cobalt Dual Catalysis. Journal of the American Chemical Society 2021, 143
(19)
, 7306-7313. https://doi.org/10.1021/jacs.1c03527
- Yik Ki Au, Jie Zhang, Yangjian Quan, Zuowei Xie. Ir-Catalyzed Selective B(3)-H Amination of o-Carboranes with NH3. Journal of the American Chemical Society 2021, 143
(11)
, 4148-4153. https://doi.org/10.1021/jacs.1c00593
- Caizhe Shi, Fusheng Li, Yuqing Chen, Shuangjie Lin, Erjun Hao, Zhuowen Guo, Urwa Tul Wosqa, Dandan Zhang, Lei Shi. Photocatalytic Umpolung Synthesis of Nucleophilic π-Allylcobalt Complexes for Allylation of Aldehydes. ACS Catalysis 2021, 11
(5)
, 2992-2998. https://doi.org/10.1021/acscatal.0c05330
- Bingquan Xia, Yanzhao Zhang, Jingrun Ran, Mietek Jaroniec, Shi-Zhang Qiao. Single-Atom Photocatalysts for Emerging Reactions. ACS Central Science 2021, 7
(1)
, 39-54. https://doi.org/10.1021/acscentsci.0c01466
- Jia-Dong Guo, Xiu-Long Yang, Bin Chen, Chen-Ho Tung, Li-Zhu Wu. Photoredox/Cobalt-Catalyzed C(sp3)–H Bond Functionalization toward Phenanthrene Skeletons with Hydrogen Evolution. Organic Letters 2020, 22
(24)
, 9627-9632. https://doi.org/10.1021/acs.orglett.0c03665
- Peng Lu, Yi Zhao, Jing Dong, Bing-Bao Mei, Xian-Long Du, Zheng Jiang, Yong-Mei Liu, He-Yong He, Yang-Dong Wang, Xue-Zhi Duan, Xing-Gui Zhou, Yong Cao. Direct and Efficient Synthesis of Clean H2O2 from CO-Assisted Aqueous O2 Reduction. ACS Catalysis 2020, 10
(23)
, 13993-14005. https://doi.org/10.1021/acscatal.0c02847
- Haidong Liu, Yi Li, Ding-Xing Wang, Meng-Meng Sun, Chao Feng. Visible-Light-Promoted Regioselective 1,3-Fluoroallylation of gem-Difluorocyclopropanes. Organic Letters 2020, 22
(21)
, 8681-8686. https://doi.org/10.1021/acs.orglett.0c03268
- Chao Zhou, Tao Lei, Xiang-Zhu Wei, Chen Ye, Zan Liu, Bin Chen, Chen-Ho Tung, Li-Zhu Wu. Metal-Free, Redox-Neutral, Site-Selective Access to Heteroarylamine via Direct Radical–Radical Cross-Coupling Powered by Visible Light Photocatalysis. Journal of the American Chemical Society 2020, 142
(39)
, 16805-16813. https://doi.org/10.1021/jacs.0c07600
- Zihang Qiu, Chao-Jun Li. Transformations of Less-Activated Phenols and Phenol Derivatives via C–O Cleavage. Chemical Reviews 2020, 120
(18)
, 10454-10515. https://doi.org/10.1021/acs.chemrev.0c00088
- Tao Lei, Ge Liang, Yuan-Yuan Cheng, Bin Chen, Chen-Ho Tung, Li-Zhu Wu. Cobaloxime Catalysis for Enamine Phosphorylation with Hydrogen Evolution. Organic Letters 2020, 22
(14)
, 5385-5389. https://doi.org/10.1021/acs.orglett.0c01709
- Xiaoyu Wang, Shengchun Wang, Yiming Gao, He Sun, Xing’an Liang, Faxiang Bu, Takfaoui Abdelilah, Aiwen Lei. Oxidant-Induced Azolation of Electron-Rich Phenol Derivatives. Organic Letters 2020, 22
(14)
, 5429-5433. https://doi.org/10.1021/acs.orglett.0c01796
- Zhi-Jun Jia, Shilong Gao, Frances H. Arnold. Enzymatic Primary Amination of Benzylic and Allylic C(sp3)–H Bonds. Journal of the American Chemical Society 2020, 142
(23)
, 10279-10283. https://doi.org/10.1021/jacs.0c03428
- Tatsuya Morofuji, Gun Ikarashi, Naokazu Kano. Photocatalytic C–H Amination of Aromatics Overcoming Redox Potential Limitations. Organic Letters 2020, 22
(7)
, 2822-2827. https://doi.org/10.1021/acs.orglett.0c00822
- Shan Tang, Yehoshoa Ben-David, David Milstein. Oxidation of Alkenes by Water with H2 Liberation. Journal of the American Chemical Society 2020, 142
(13)
, 5980-5984. https://doi.org/10.1021/jacs.0c01592
- Mohit Kumar, Rishabh Sharma, Raziullah, Afsar Ali Khan, Ashfaq Ahmad, Himangsu Sekhar Dutta, Dipankar Koley. Cu(II)-Catalyzed Ortho C(sp2)–H Diarylamination of Arylamines To Synthesize Triarylamines. Organic Letters 2020, 22
(6)
, 2152-2156. https://doi.org/10.1021/acs.orglett.0c00196
- Qi Xu, Baihui Zheng, Xiaoxuan Zhou, Ling Pan, Qun Liu, Yifei Li. Photoinduced C(sp2)–H/C(sp2)–H Cross-Coupling of Alkenes: Direct Synthesis of 1,3-Dienes. Organic Letters 2020, 22
(5)
, 1692-1697. https://doi.org/10.1021/acs.orglett.9b04201
- Jie Wang, Yu-Bo Pang, Na Tao, Runsheng Zeng, Yingsheng Zhao. Nickel-Catalyzed, para-Selective, Radical-Based Alkylation of Aromatic Ketones. Organic Letters 2020, 22
(3)
, 854-857. https://doi.org/10.1021/acs.orglett.9b04327
- Nengchao Luo, Tingting Hou, Shiyang Liu, Bin Zeng, Jianmin Lu, Jian Zhang, Hongji Li, Feng Wang. Photocatalytic Coproduction of Deoxybenzoin and H2 through Tandem Redox Reactions. ACS Catalysis 2020, 10
(1)
, 762-769. https://doi.org/10.1021/acscatal.9b03651
- Cheng Huang, Jing-Hao Wang, Jia Qiao, Xiu-Wei Fan, Bin Chen, Chen-Ho Tung, Li-Zhu Wu. Direct Arylation of Unactivated Alkanes with Heteroarenes by Visible-Light Catalysis. The Journal of Organic Chemistry 2019, 84
(20)
, 12904-12912. https://doi.org/10.1021/acs.joc.9b01603
- Taoyuan Liang, He Zhao, Lingzhen Gong, Huanfeng Jiang, Min Zhang. Direct Access to Functionalized Indoles via Single Electron Oxidation Induced Coupling of Diarylamines with 1,3-Dicarbonyl Compounds. Organic Letters 2019, 21
(17)
, 6736-6740. https://doi.org/10.1021/acs.orglett.9b02349
- Wen-Qiang Liu, Tao Lei, Shuai Zhou, Xiu-Long Yang, Jian Li, Bin Chen, Jayaraman Sivaguru, Chen-Ho Tung, Li-Zhu Wu. Cobaloxime Catalysis: Selective Synthesis of Alkenylphosphine Oxides under Visible Light. Journal of the American Chemical Society 2019, 141
(35)
, 13941-13947. https://doi.org/10.1021/jacs.9b06920
- Jing-Hao Wang, Tao Lei, Xiao-Lei Nan, Hao-Lin Wu, Xu-Bing Li, Bin Chen, Chen-Ho Tung, Li-Zhu Wu. Regioselective Ortho Amination of an Aromatic C–H Bond by Trifluoroacetic Acid via Electrochemistry. Organic Letters 2019, 21
(14)
, 5581-5585. https://doi.org/10.1021/acs.orglett.9b01910
- Lin Yu, Chan Yang, Yongqi Yu, Da Liu, Liang Hu, Yuanjiu Xiao, Ze-Nan Song, Ze Tan. Ammonia as Ultimate Amino Source in Synthesis of Primary Amines via Nickel-Promoted C–H Bond Amination. Organic Letters 2019, 21
(14)
, 5634-5638. https://doi.org/10.1021/acs.orglett.9b01968
- Huamin Wang, Xinlong Gao, Zongchao Lv, Takfaoui Abdelilah, Aiwen Lei. Recent Advances in Oxidative R1-H/R2-H Cross-Coupling with Hydrogen Evolution via Photo-/Electrochemistry. Chemical Reviews 2019, 119
(12)
, 6769-6787. https://doi.org/10.1021/acs.chemrev.9b00045
- Wenbo Liu, Jianbin Li, Pierre Querard, Chao-Jun Li. Transition-Metal-Free C–C, C–O, and C–N Cross-Couplings Enabled by Light. Journal of the American Chemical Society 2019, 141
(16)
, 6755-6764. https://doi.org/10.1021/jacs.9b02684
- Zongbin Jia, Qi Yang, Long Zhang, Sanzhong Luo. Photoredox Mediated Acceptorless Dehydrogenative Coupling of Saturated N-Heterocycles. ACS Catalysis 2019, 9
(4)
, 3589-3594. https://doi.org/10.1021/acscatal.9b00123
- Fengqian Zhao, Qiong Yang, Jingjie Zhang, Weimin Shi, Huanhuan Hu, Fang Liang, Wei Wei, Shaolin Zhou. Photocatalytic Hydrogen-Evolving Cross-Coupling of Arenes with Primary Amines. Organic Letters 2018, 20
(24)
, 7753-7757. https://doi.org/10.1021/acs.orglett.8b03089
- Hui Cao, Heming Jiang, Hongyu Feng, Jeric Mun Chung Kwan, Xiaogang Liu, Jie Wu. Photo-induced Decarboxylative Heck-Type Coupling of Unactivated Aliphatic Acids and Terminal Alkenes in the Absence of Sacrificial Hydrogen Acceptors. Journal of the American Chemical Society 2018, 140
(47)
, 16360-16367. https://doi.org/10.1021/jacs.8b11218
- Jingyu Cai, Min Zhang, Dengke Wang, Zhaohui Li. Engineering Surface Wettability of Reduced Graphene Oxide To Realize Efficient Interfacial Photocatalytic Benzene Hydroxylation in Water. ACS Sustainable Chemistry & Engineering 2018, 6
(11)
, 15682-15687. https://doi.org/10.1021/acssuschemeng.8b04175
- Huamin Wang, Yongli Li, Zilu Tang, Shengchun Wang, Heng Zhang, Hengjiang Cong, Aiwen Lei. Z-Selective Addition of Diaryl Phosphine Oxides to Alkynes via Photoredox Catalysis. ACS Catalysis 2018, 8
(11)
, 10599-10605. https://doi.org/10.1021/acscatal.8b02617
- Hyunwoo Kim, Joon Heo, Junho Kim, Mu-Hyun Baik, Sukbok Chang. Copper-Mediated Amination of Aryl C–H Bonds with the Direct Use of Aqueous Ammonia via a Disproportionation Pathway. Journal of the American Chemical Society 2018, 140
(43)
, 14350-14356. https://doi.org/10.1021/jacs.8b08826
- Shan Tang, Li Zeng, Aiwen Lei. Oxidative R1–H/R2–H Cross-Coupling with Hydrogen Evolution. Journal of the American Chemical Society 2018, 140
(41)
, 13128-13135. https://doi.org/10.1021/jacs.8b07327
- Bin Chen, Li-Zhu Wu, Chen-Ho Tung. Photocatalytic Activation of Less Reactive Bonds and Their Functionalization via Hydrogen-Evolution Cross-Couplings. Accounts of Chemical Research 2018, 51
(10)
, 2512-2523. https://doi.org/10.1021/acs.accounts.8b00267
- Meng Yu, Tao Zhang, Hitesh B. Jalani, Xunqing Dong, Hongjian Lu, Guigen Li. Iridium-Catalyzed Aryl C–H Sulfonamidation and Amide Formation Using a Bifunctional Nitrogen Source. Organic Letters 2018, 20
(16)
, 4828-4832. https://doi.org/10.1021/acs.orglett.8b01977
- Manoj
K. Sahoo, Krishnasamy Saravanakumar, Garima Jaiswal, Ekambaram Balaraman. Photocatalysis Enabling Acceptorless Dehydrogenation of Diaryl Hydrazines at Room Temperature. ACS Catalysis 2018, 8
(8)
, 7727-7733. https://doi.org/10.1021/acscatal.8b01579
- Shuguang Zhou, Bi-Wei Yan, Shuai-Xin Fan, Jie-Sheng Tian, Teck-Peng Loh. Regioselective Formal [4 + 2] Cycloadditions of Enaminones with Diazocarbonyls through RhIII-Catalyzed C–H Bond Functionalization. Organic Letters 2018, 20
(13)
, 3975-3979. https://doi.org/10.1021/acs.orglett.8b01540
- Xiu-Long Yang, Jia-Dong Guo, Tao Lei, Bin Chen, Chen-Ho Tung, Li-Zhu Wu. Oxidative Cyclization Synthesis of Tetrahydroquinolines and Reductive Hydrogenation of Maleimides under Redox-Neutral Conditions. Organic Letters 2018, 20
(10)
, 2916-2920. https://doi.org/10.1021/acs.orglett.8b00977
- Ailong Shao, Jirui Zhan, Na Li, Chien-Wei Chiang, Aiwen Lei. External Oxidant-Free Dehydrogenative Lactonization of 2-Arylbenzoic Acids via Visible-Light Photocatalysis. The Journal of Organic Chemistry 2018, 83
(7)
, 3582-3589. https://doi.org/10.1021/acs.joc.7b03195
- Taoyuan Liang, Zhenda Tan, He Zhao, Xiuwen Chen, Huanfeng Jiang, and Min Zhang . Aerobic Copper-Catalyzed Synthesis of Benzimidazoles from Diaryl- and Alkylamines via Tandem Triple C–H Aminations. ACS Catalysis 2018, 8
(3)
, 2242-2246. https://doi.org/10.1021/acscatal.8b00082
- Yong Wu, Hong Yi, and Aiwen Lei . Electrochemical Acceptorless Dehydrogenation of N-Heterocycles Utilizing TEMPO as Organo-Electrocatalyst. ACS Catalysis 2018, 8
(2)
, 1192-1196. https://doi.org/10.1021/acscatal.7b04137
- Laura Elena Hofmann, Leonard Mach, and Markus R. Heinrich . Nitrogen Oxides and Nitric Acid Enable the Sustainable Hydroxylation and Nitrohydroxylation of Benzenes under Visible Light Irradiation. The Journal of Organic Chemistry 2018, 83
(1)
, 431-436. https://doi.org/10.1021/acs.joc.7b02333
- Nagnath Yadav More, Kishor Padala, and Masilamani Jeganmohan . Ruthenium-Catalyzed C–H Benzoxylation of tert-Benzamides with Aromatic Acids by Weak Coordination. The Journal of Organic Chemistry 2017, 82
(23)
, 12691-12700. https://doi.org/10.1021/acs.joc.7b02495
- Linbin Niu, Jiamei Liu, Hong Yi, Shengchun Wang, Xing-An Liang, Atul K. Singh, Chien-Wei Chiang, and Aiwen Lei . Visible-Light-Induced External Oxidant-Free Oxidative Phosphonylation of C(sp2)–H Bonds. ACS Catalysis 2017, 7
(11)
, 7412-7416. https://doi.org/10.1021/acscatal.7b02418
- Markus D. Kärkäs . Photochemical Generation of Nitrogen-Centered Amidyl, Hydrazonyl, and Imidyl Radicals: Methodology Developments and Catalytic Applications. ACS Catalysis 2017, 7
(8)
, 4999-5022. https://doi.org/10.1021/acscatal.7b01385
- Hong Yi, Guoting Zhang, Huamin Wang, Zhiyuan Huang, Jue Wang, Atul K. Singh, and Aiwen Lei . Recent Advances in Radical C–H Activation/Radical Cross-Coupling. Chemical Reviews 2017, 117
(13)
, 9016-9085. https://doi.org/10.1021/acs.chemrev.6b00620
- Yan Qin, Lihui Zhu, and Sanzhong Luo . Organocatalysis in Inert C–H Bond Functionalization. Chemical Reviews 2017, 117
(13)
, 9433-9520. https://doi.org/10.1021/acs.chemrev.6b00657
- Ming Xiang, Zhi-Kun Xin, Bin Chen, Chen-Ho Tung, and Li-Zhu Wu . Exploring the Reducing Ability of Organic Dye (Acr+-Mes) for Fluorination and Oxidation of Benzylic C(sp3)–H Bonds under Visible Light Irradiation. Organic Letters 2017, 19
(11)
, 3009-3012. https://doi.org/10.1021/acs.orglett.7b01270
- Yi-Wen Zheng, Pan Ye, Bin Chen, Qing-Yuan Meng, Ke Feng, Wenguang Wang, Li-Zhu Wu, and Chen-Ho Tung . Benzene C–H Etherification via Photocatalytic Hydrogen-Evolution Cross-Coupling Reaction. Organic Letters 2017, 19
(9)
, 2206-2209. https://doi.org/10.1021/acs.orglett.7b00463
- Yating Zhao, Binbin Huang, Chao Yang, Bing Li, Baoquan Gou, and Wujiong Xia . Photocatalytic Cross-Dehydrogenative Amination Reactions between Phenols and Diarylamines. ACS Catalysis 2017, 7
(4)
, 2446-2451. https://doi.org/10.1021/acscatal.7b00192
- Hyunwoo Kim and Sukbok Chang . The Use of Ammonia as an Ultimate Amino Source in the Transition Metal-Catalyzed C–H Amination. Accounts of Chemical Research 2017, 50
(3)
, 482-486. https://doi.org/10.1021/acs.accounts.6b00489
- Hong Yi, Linbin Niu, Shengchun Wang, Tianyi Liu, Atul K. Singh, and Aiwen Lei . Visible-Light-Induced Acetalization of Aldehydes with Alcohols. Organic Letters 2017, 19
(1)
, 122-125. https://doi.org/10.1021/acs.orglett.6b03403
- Jianye Zhang, Zhaoliang Yang, Chunlei Liu, Hao Wan, Zizhao Hao, Xinrui Ji, Pengjie Wang, Hong Yi, Aiwen Lei. Tailoring photocatalysts to modulate oxidative potential of anilides enhances para-selective electrochemical hydroxylation. Nature Communications 2024, 15
(1)
https://doi.org/10.1038/s41467-024-51327-4
- Jinghao Wang, Caoyu Yang, Huiwen Gao, Lulu Zuo, Zhiyu Guo, Pengqi Yang, Siyang Li, Zhiyong Tang. Customized Photoelectrochemical C−N and C−P Bond Formation Enabled by Tailored Deposition on Photoanodes. Angewandte Chemie 2024, 136
(41)
https://doi.org/10.1002/ange.202408901
- Weimei Zeng, Youai Qiu. Electrochemical conversion of organic compounds and inorganic small molecules. Science China Chemistry 2024, 67
(10)
, 3223-3246. https://doi.org/10.1007/s11426-024-2036-0
- Jingwen Wei, Thong Pham, Emmanuel Ifeanyi Attah, Mengjia Liu, Timothy Yaroshuk, Hao Chen, Lukasz Wojtas, Xiaodong Shi. Gold‐Catalyzed Diyne‐Ene Annulation for the Synthesis of Polysubstituted Benzenes through Formal [3+3] Approach with Amide as the Critical Co‐Catalyst. Angewandte Chemie 2024, 136
(39)
https://doi.org/10.1002/ange.202407360
- Donghan Liu, Ting Tu, Tinglei Zhang, Guihua Nie, Tianhui Liao, Shi‐Chao Ren, Xinglong Zhang, Yonggui Robin Chi. Photocatalytic Direct
Para
‐Selective C−H Amination of Benzyl Alcohols: Selectivity Independent of Side Substituents. Angewandte Chemie 2024, 145 https://doi.org/10.1002/ange.202407293
- Donghan Liu, Ting Tu, Tinglei Zhang, Guihua Nie, Tianhui Liao, Shi‐Chao Ren, Xinglong Zhang, Yonggui Robin Chi. Photocatalytic Direct
Para
‐Selective C−H Amination of Benzyl Alcohols: Selectivity Independent of Side Substituents. Angewandte Chemie International Edition 2024, 145 https://doi.org/10.1002/anie.202407293
- Jinghao Wang, Caoyu Yang, Huiwen Gao, Lulu Zuo, Zhiyu Guo, Pengqi Yang, Siyang Li, Zhiyong Tang. Customized Photoelectrochemical C−N and C−P Bond Formation Enabled by Tailored Deposition on Photoanodes. Angewandte Chemie International Edition 2024, https://doi.org/10.1002/anie.202408901
- Zhan‐Lin Wang, Jin‐Kai Cheng, Fei Wang. Iron‐catalyzed C‐7 Selective NH
2
Amination of Indoles. Angewandte Chemie 2024, 62 https://doi.org/10.1002/ange.202412103
- Zhan‐Lin Wang, Jin‐Kai Cheng, Fei Wang. Iron‐catalyzed C‐7 Selective NH
2
Amination of Indoles. Angewandte Chemie International Edition 2024, 62 https://doi.org/10.1002/anie.202412103
- Jingwen Wei, Thong Pham, Emmanuel Ifeanyi Attah, Mengjia Liu, Timothy Yaroshuk, Hao Chen, Lukasz Wojtas, Xiaodong Shi. Gold‐Catalyzed Diyne‐Ene Annulation for the Synthesis of Polysubstituted Benzenes through Formal [3+3] Approach with Amide as the Critical Co‐Catalyst. Angewandte Chemie International Edition 2024, 17 https://doi.org/10.1002/anie.202407360
- Phong Dam, Kaiming Zuo, Luis Miguel Azofra, Osama El‐Sepelgy. Biomimetic Photoexcited Cobaloxime Catalysis in Organic Synthesis. Angewandte Chemie 2024, 136
(33)
https://doi.org/10.1002/ange.202405775
- Phong Dam, Kaiming Zuo, Luis Miguel Azofra, Osama El‐Sepelgy. Biomimetic Photoexcited Cobaloxime Catalysis in Organic Synthesis. Angewandte Chemie International Edition 2024, 63
(33)
https://doi.org/10.1002/anie.202405775
- Yuanyuan Yue, Xiaohui Guo, Jianhang Zhang, Zhiqiang Zhang, Yilin Zhang, Qinghu Tang, Ruopeng Bai, Hong Yi, Jianming Liu. Electrochemical Oxidation Enables Radical Dearomative Spiroannulation to 2
H
‐Spiro[benzofuran‐3,9′‐fluoren]‐2‐one. Chemistry – A European Journal 2024, 30
(43)
https://doi.org/10.1002/chem.202401303
- Qingxi Meng, Fen Wang. Theoretical investigations of Co-catalyzed allylic aminations. Molecular Catalysis 2024, 564 , 114342. https://doi.org/10.1016/j.mcat.2024.114342
- Hoonchul Choi, Won Seok Ham, Pit van Bonn, Jianbo Zhang, Dongwook Kim, Sukbok Chang. Mechanistic Approach Toward the C4‐Selective Amination of Pyridines via Nucleophilic Substitution of Hydrogen. Angewandte Chemie International Edition 2024, 63
(24)
https://doi.org/10.1002/anie.202401388
- Hoonchul Choi, Won Seok Ham, Pit van Bonn, Jianbo Zhang, Dongwook Kim, Sukbok Chang. Mechanistic Approach Toward the C4‐Selective Amination of Pyridines via Nucleophilic Substitution of Hydrogen. Angewandte Chemie 2024, 136
(24)
https://doi.org/10.1002/ange.202401388
- Chao-Rui Ma, Guan-Wang Huang, Hui Xu, Zhan-Lin Wang, Zheng-Hao Li, Jun Liu, Yin Yang, Gongyu Li, Yanfeng Dang, Fei Wang. Site-selective arene C–H amination with iron-aminyl radical. Nature Catalysis 2024, 7
(6)
, 636-645. https://doi.org/10.1038/s41929-024-01140-5
- Pei-Ting Li, Zi-Fa Shi, Wei Yu. Cyclization reactions of 1,6-dienes and 1,6-enynes by dual cobalt photocatalysis. Organic Chemistry Frontiers 2024, 11
(11)
, 3048-3057. https://doi.org/10.1039/D4QO00311J
- Kunpeng Teng, Qian Liu, Jie Lv, TingTing Li. The application of nitroarenes in catalyst‐free photo‐driven reactions. ChemPhotoChem 2024, 8
(4)
https://doi.org/10.1002/cptc.202300236
- Yu-Feng Ren, Xiao-Yi Chen, Hai-Wu Du, Wei Shu. Arylamine synthesis enabled by a photocatalytic skeletal-editing dehydrogenative aromatization strategy. Chem Catalysis 2024, 4
(1)
, 100873. https://doi.org/10.1016/j.checat.2023.100873
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.