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Catalyst Control of Site Selectivity in the PdII/IV-Catalyzed Direct Arylation of Naphthalene

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Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, United States
Cite this: ACS Catal. 2011, 1, 3, 170–174
Publication Date (Web):January 25, 2011
https://doi.org/10.1021/cs1001543
Copyright © 2011 American Chemical Society

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    Abstract

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    This letter describes a new method for the highly site- and chemoselective Pd-catalyzed direct arylation of naphthalene. Tuning the structure of the diimine-ligated Pd catalyst results in formation of the α-arylated product in high yield and >50:1 selectivity. This is, to our knowledge, the first systematic evaluation of catalyst control in the C−H arylation of an unactivated aromatic substrate. Preliminary studies implicate an unusual mechanism involving sequential naphthalene π-coordination/metalation at PdIV.

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    Complete experimental details, catalyst characterization, and kinetic data are provided. This material is available free of charge via the Internet at http://pubs.acs.org.

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    2. 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
    3. Iain A. Stepek, Kenichiro Itami. Recent Advances in C–H Activation for the Synthesis of π-Extended Materials. ACS Materials Letters 2020, 2 (8) , 951-974. https://doi.org/10.1021/acsmaterialslett.0c00206
    4. Hong-Yan Hao, Yang-Jie Mao, Zhen-Yuan Xu, Shao-Jie Lou, Dan-Qian Xu. Selective Cross-Dehydrogenative C(sp3)–H Arylation with Arenes. Organic Letters 2020, 22 (6) , 2396-2402. https://doi.org/10.1021/acs.orglett.0c00588
    5. Arup Mondal, Hao Chen, Lea Flämig, Philipp Wedi, Manuel van Gemmeren. Sterically Controlled Late-Stage C–H Alkynylation of Arenes. Journal of the American Chemical Society 2019, 141 (47) , 18662-18667. https://doi.org/10.1021/jacs.9b10868
    6. Jae Bin Lee, Min Ho Jeon, Jeong Kon Seo, Gert von Helden, Jan-Uwe Rohde, Bum Suk Zhao, Jongcheol Seo, Sung You Hong. Annulative π-Extension of Unactivated Benzene Derivatives through Nondirected C–H Arylation. Organic Letters 2019, 21 (17) , 7004-7008. https://doi.org/10.1021/acs.orglett.9b02583
    7. Henry H. Wilson, Connor A. Koellner, Zain M. Hannan, Caroline B. Endy, Mark W. Bezpalko, Nicholas A. Piro, W. Scott Kassel, Matthew D. Sonntag, Christopher R. Graves. Synthesis and Characterization of Neutral Ligand α-Diimine Complexes of Aluminum with Tunable Redox Energetics. Inorganic Chemistry 2018, 57 (16) , 9622-9633. https://doi.org/10.1021/acs.inorgchem.8b00045
    8. Mari Shibata, Hideto Ito, and Kenichiro Itami . C–H Arylation of Phenanthrene with Trimethylphenylsilane by Pd/o-Chloranil Catalysis: Computational Studies on the Mechanism, Regioselectivity, and Role of o-Chloranil. Journal of the American Chemical Society 2018, 140 (6) , 2196-2205. https://doi.org/10.1021/jacs.7b11260
    9. Lei Zhang and De-Cai Fang . Key Role of PdIV Intermediates in Promoting PdII-Catalyzed Dehydrogenative Homocoupling of Two Arenes: A DFT Study. Organometallics 2017, 36 (24) , 4943-4951. https://doi.org/10.1021/acs.organomet.7b00778
    10. Lujia Mao, Rüdiger Bertermann, Simon G. Rachor, Kálmán J. Szabó, and Todd B. Marder . Palladium-Catalyzed Oxidative Borylation of Allylic C–H Bonds in Alkenes. Organic Letters 2017, 19 (24) , 6590-6593. https://doi.org/10.1021/acs.orglett.7b03296
    11. Jaewoon Kim and Soon Hyeok Hong . Ligand-Promoted Direct C–H Arylation of Simple Arenes: Evidence for a Cooperative Bimetallic Mechanism. ACS Catalysis 2017, 7 (5) , 3336-3343. https://doi.org/10.1021/acscatal.7b00397
    12. Yu-Xin Luan, Tao Zhang, Wei-Wei Yao, Ke Lu, Lu-Yao Kong, Yu-Tong Lin, and Mengchun Ye . Amide-Ligand-Controlled Highly para-Selective Arylation of Monosubstituted Simple Arenes with Arylboronic Acids. Journal of the American Chemical Society 2017, 139 (5) , 1786-1789. https://doi.org/10.1021/jacs.6b12907
    13. Yajie Fu, Panpan Wang, Xin Guo, Ping Wu, Xu Meng, and Baohua Chen . Synthesis of Polyfunctional Pyridines via Copper-Catalyzed Oxidative Coupling Reactions. The Journal of Organic Chemistry 2016, 81 (23) , 11671-11677. https://doi.org/10.1021/acs.joc.6b02081
    14. Shrikant M. Khake, Rahul A. Jagtap, Yuvraj B. Dangat, Rajesh G. Gonnade, Kumar Vanka, and Benudhar Punji . Mechanistic Insights into Pincer-Ligated Palladium-Catalyzed Arylation of Azoles with Aryl Iodides: Evidence of a PdII–PdIV–PdII Pathway. Organometallics 2016, 35 (6) , 875-886. https://doi.org/10.1021/acs.organomet.6b00003
    15. Shengfei Jin, Chongguo Jiang, Xiaoshi Peng, Chunhui Shan, Shanshan Cui, Yuanyuan Niu, Yang Liu, Yu Lan, Yongxiang Liu, and Maosheng Cheng . Gold(I)-Catalyzed Angle Strain Controlled Strategy to Furopyran Derivatives from Propargyl Vinyl Ethers: Insight into the Regioselectivity of Cycloisomerization. Organic Letters 2016, 18 (4) , 680-683. https://doi.org/10.1021/acs.orglett.5b03641
    16. Bao-Tian Luo, Huan Liu, Zhi-Jie Lin, Jingxing Jiang, Dong-Sheng Shen, Rui-Zhi Liu, Zhuofeng Ke, and Feng-Shou Liu . Aerobic and Efficient Direct Arylation of Five-Membered Heteroarenes and Their Benzocondensed Derivatives with Aryl Bromides by Bulky α-Hydroxyimine Palladium Complexes. Organometallics 2015, 34 (20) , 4881-4894. https://doi.org/10.1021/acs.organomet.5b00181
    17. Pan Gao, Wei Guo, Jingjing Xue, Yue Zhao, Yu Yuan, Yuanzhi Xia, and Zhuangzhi Shi . Iridium(III)-Catalyzed Direct Arylation of C–H Bonds with Diaryliodonium Salts. Journal of the American Chemical Society 2015, 137 (38) , 12231-12240. https://doi.org/10.1021/jacs.5b06758
    18. Yang Yang and Peng Liu . Mechanism and Origins of Selectivities in the Copper-Catalyzed Dearomatization-Induced ortho C–H Cyanation of Vinylarenes. ACS Catalysis 2015, 5 (5) , 2944-2951. https://doi.org/10.1021/acscatal.5b00443
    19. Masahito Murai, Keishi Takami, Hirotaka Takeshima, and Kazuhiko Takai . Iridium-Catalyzed Dehydrogenative Silylation of Azulenes Based on Regioselective C–H Bond Activation. Organic Letters 2015, 17 (7) , 1798-1801. https://doi.org/10.1021/acs.orglett.5b00575
    20. Allan J. Canty, Alireza Ariafard, Brian F. Yates, and Melanie S. Sanford . Computational Study of Intramolecular Arene Palladation at a Palladium(IV) Center. Organometallics 2015, 34 (6) , 1085-1090. https://doi.org/10.1021/om5013049
    21. Yan-Mei Xing, Lei Zhang, and De-Cai Fang . DFT Studies on the Mechanism of Palladium(IV)-Mediated C–H Activation Reactions: Oxidant Effect and Regioselectivity. Organometallics 2015, 34 (4) , 770-777. https://doi.org/10.1021/om501239n
    22. Miki Iyanaga, Yoshinori Aihara, and Naoto Chatani . Direct Arylation of C(sp3)–H Bonds in Aliphatic Amides with Diaryliodonium Salts in the Presence of a Nickel Catalyst. The Journal of Organic Chemistry 2014, 79 (24) , 11933-11939. https://doi.org/10.1021/jo501691f
    23. Pengfei Li, Guolin Cheng, Hong Zhang, Xianxiang Xu, Jingyuan Gao, and Xiuling Cui . Copper-Catalyzed One-Pot Synthesis of Unsymmetrical Arylurea Derivatives via Tandem Reaction of Diaryliodonium Salts with N-Arylcyanamide. The Journal of Organic Chemistry 2014, 79 (17) , 8156-8162. https://doi.org/10.1021/jo501334u
    24. Lehao Huang, Xudong Sun, Qian Li, and Chenze Qi . Palladium-Catalyzed C8 Alkylation of 1-Naphthylamides with Alkyl Halides via Bidentate-Chelation Assistance. The Journal of Organic Chemistry 2014, 79 (14) , 6720-6725. https://doi.org/10.1021/jo500932x
    25. Devin M. Ferguson, Stacey R. Rudolph, and Dipannita Kalyani . Palladium-Catalyzed Intra- and Intermolecular C–H Arylation Using Mesylates: Synthetic Scope and Mechanistic Studies. ACS Catalysis 2014, 4 (7) , 2395-2401. https://doi.org/10.1021/cs500587b
    26. Ádám Sinai, Ádám Mészáros, Tamás Gáti, Veronika Kudar, Anna Palló, and Zoltán Novák . Copper-Catalyzed Oxidative Ring Closure and Carboarylation of 2-Ethynylanilides. Organic Letters 2013, 15 (22) , 5654-5657. https://doi.org/10.1021/ol402600r
    27. Anna M. Wagner, Amanda J. Hickman, and Melanie S. Sanford . Platinum-Catalyzed C–H Arylation of Simple Arenes. Journal of the American Chemical Society 2013, 135 (42) , 15710-15713. https://doi.org/10.1021/ja408112j
    28. Keary M. Engle and Jin-Quan Yu . Developing Ligands for Palladium(II)-Catalyzed C–H Functionalization: Intimate Dialogue between Ligand and Substrate. The Journal of Organic Chemistry 2013, 78 (18) , 8927-8955. https://doi.org/10.1021/jo400159y
    29. Bing Lian, Lei Zhang, Gregory Adam Chass, and De-Cai Fang . Pd(OAc)2-Catalyzed C–H Activation/C–O Cyclization: Mechanism, Role of Oxidant—Probed by Density Functional Theory. The Journal of Organic Chemistry 2013, 78 (17) , 8376-8385. https://doi.org/10.1021/jo4010712
    30. Ansis Maleckis, Jeff W. Kampf, and Melanie S. Sanford . A Detailed Study of Acetate-Assisted C–H Activation at Palladium(IV) Centers. Journal of the American Chemical Society 2013, 135 (17) , 6618-6625. https://doi.org/10.1021/ja401557m
    31. Lehao Huang, Qian Li, Chen Wang, and Chenze Qi . Palladium(II)-Catalyzed Regioselective Arylation of Naphthylamides with Aryl Iodides Utilizing a Quinolinamide Bidentate System. The Journal of Organic Chemistry 2013, 78 (7) , 3030-3038. https://doi.org/10.1021/jo400017v
    32. Thomas E. Storr and Michael F. Greaney . Palladium-Catalyzed Arylation of Simple Arenes with Iodonium Salts. Organic Letters 2013, 15 (6) , 1410-1413. https://doi.org/10.1021/ol400412z
    33. Evan E. Joslin, Claire L. McMullin, T. Brent Gunnoe, Thomas R. Cundari, Michal Sabat, and William H. Myers . Catalytic Hydroarylation of Ethylene Using TpRu(L)(NCMe)Ph (L = 2,6,7-Trioxa-1-phosphabicyclo[2,2,1]heptane): Comparison to TpRu(L′)(NCMe)Ph Systems (L′ = CO, PMe3, P(pyr)3, or P(OCH2)3CEt). Organometallics 2012, 31 (19) , 6851-6860. https://doi.org/10.1021/om300676e
    34. Alban Petit, Josh Flygare, Alex T. Miller, Gerrit Winkel, and Daniel H. Ess . Transition-State Metal Aryl Bond Stability Determines Regioselectivity in Palladium Acetate Mediated C–H Bond Activation of Heteroarenes. Organic Letters 2012, 14 (14) , 3680-3683. https://doi.org/10.1021/ol301521n
    35. Sharon R. Neufeldt and Melanie S. Sanford . Controlling Site Selectivity in Palladium-Catalyzed C–H Bond Functionalization. Accounts of Chemical Research 2012, 45 (6) , 936-946. https://doi.org/10.1021/ar300014f
    36. Wei-Chun Shih, Wen-Ching Chen, Ying-Chieh Lai, Ming-Shiuan Yu, Jhao-Jhe Ho, Glenn P. A. Yap, and Tiow-Gan Ong . The Regioselective Switch for Amino-NHC Mediated C–H Activation of Benzimidazole via Ni–Al Synergistic Catalysis. Organic Letters 2012, 14 (8) , 2046-2049. https://doi.org/10.1021/ol300570f
    37. Ryan D. Baxter, David Sale, Keary M. Engle, Jin-Quan Yu, and Donna G. Blackmond . Mechanistic Rationalization of Unusual Kinetics in Pd-Catalyzed C–H Olefination. Journal of the American Chemical Society 2012, 134 (10) , 4600-4606. https://doi.org/10.1021/ja207634t
    38. Amanda J. Hickman, Megan A. Cismesia, and Melanie S. Sanford . Structure Activity Relationship Study of Diimine PtII Catalysts for H/D Exchange. Organometallics 2012, 31 (5) , 1761-1766. https://doi.org/10.1021/om201105b
    39. Ansis Maleckis and Melanie S. Sanford . Facial Tridentate Ligands for Stabilizing Palladium(IV) Complexes. Organometallics 2011, 30 (24) , 6617-6627. https://doi.org/10.1021/om200779j
    40. Tae-Hong Park, Amanda J. Hickman, Kyoungmoo Koh, Stephen Martin, Antek G. Wong-Foy, Melanie S. Sanford, and Adam J. Matzger . Highly Dispersed Palladium(II) in a Defective Metal–Organic Framework: Application to C–H Activation and Functionalization. Journal of the American Chemical Society 2011, 133 (50) , 20138-20141. https://doi.org/10.1021/ja2094316
    41. Frederic W. Patureau, Corinna Nimphius, and Frank Glorius . Rh Catalyzed C–H Activation and Oxidative Olefination without Chelate Assistance: On the Reactivity of Bromoarenes. Organic Letters 2011, 13 (24) , 6346-6349. https://doi.org/10.1021/ol202557w
    42. Joy M. Racowski, Nicholas D. Ball, and Melanie S. Sanford . C–H Bond Activation at Palladium(IV) Centers. Journal of the American Chemical Society 2011, 133 (45) , 18022-18025. https://doi.org/10.1021/ja2051099
    43. Xisheng Wang, Dasheng Leow, and Jin-Quan Yu . Pd(II)-Catalyzed para-Selective C–H Arylation of Monosubstituted Arenes. Journal of the American Chemical Society 2011, 133 (35) , 13864-13867. https://doi.org/10.1021/ja206572w
    44. Ke‐Zuan Deng, Verena Sukowski, M. Ángeles Fernández‐Ibáñez. Non‐Directed C−H Arylation of Anisole Derivatives via Pd/S,O‐Ligand Catalysis. Angewandte Chemie International Edition 2024, 63 (19) https://doi.org/10.1002/anie.202400689
    45. Ke‐Zuan Deng, Verena Sukowski, M. Ángeles Fernández‐Ibáñez. Non‐Directed C−H Arylation of Anisole Derivatives via Pd/S,O‐Ligand Catalysis. Angewandte Chemie 2024, 136 (19) https://doi.org/10.1002/ange.202400689
    46. Yaqi Zhang, Shengxiang Qin, Bendu Pan, Rihui Cao, Raymond Wai‐Yin Sun, Liqin Qiu. Nickel‐Catalyzed Intermolecular Branched/Linear Regioselective C−H Alkylation of 4‐Oxoquinazolines. Advanced Synthesis & Catalysis 2023, 365 (4) , 469-475. https://doi.org/10.1002/adsc.202201353
    47. Petros L. Gkizis. Photochemical Cross‐Coupling Enables Csp 3 −C Bond Formation by C−H Homolytic Cleavage: New Developments and Perspectives. European Journal of Organic Chemistry 2022, 2022 (46) https://doi.org/10.1002/ejoc.202201139
    48. Verena Sukowski, Manuela van Borselen, Simon Mathew, M. Ángeles Fernández‐Ibáñez. S,O‐Ligand Promoted meta ‐C−H Arylation of Anisole Derivatives via Palladium/Norbornene Catalysis. Angewandte Chemie International Edition 2022, 61 (31) https://doi.org/10.1002/anie.202201750
    49. Verena Sukowski, Manuela van Borselen, Simon Mathew, M. Ángeles Fernández‐Ibáñez. S,O‐Ligand Promoted meta ‐C−H Arylation of Anisole Derivatives via Palladium/Norbornene Catalysis. Angewandte Chemie 2022, 134 (31) https://doi.org/10.1002/ange.202201750
    50. Samata E. Shetgaonkar, Aleena Raju, Hideyasu China, Naoko Takenaga, Toshifumi Dohi, Fateh V. Singh. Non-Palladium-Catalyzed Oxidative Coupling Reactions Using Hypervalent Iodine Reagents. Frontiers in Chemistry 2022, 10 https://doi.org/10.3389/fchem.2022.909250
    51. Shubhendu S. Karandikar, David R. Stuart. Refining boron–iodane exchange to access versatile arylation reagents. Chemical Communications 2022, 58 (8) , 1211-1214. https://doi.org/10.1039/D1CC06341C
    52. Tanmoy Mandal, Sudha Yadav, Joyanta Choudhury. Steric effect of NHC ligands in Pd(II)–NHC-catalyzed non-directed C–H acetoxylation of simple arenes. Journal of Organometallic Chemistry 2021, 953 , 122047. https://doi.org/10.1016/j.jorganchem.2021.122047
    53. Saumitra Sengupta, Parthasarathi Das. C–H activation reactions of nitroarenes: current status and outlook. Organic & Biomolecular Chemistry 2021, 19 (39) , 8409-8424. https://doi.org/10.1039/D1OB01455B
    54. Bodala Varaprasad, Karasala Bharat Kumar, Vidavalur Siddaiah, Pulipaka Shyamala, Lekkala Chinnari. Copper-catalyzed efficient access to 2,4,6-triphenyl pyridines via oxidative decarboxylative coupling of aryl acetic acids with oxime acetates. New Journal of Chemistry 2021, 45 (34) , 15205-15209. https://doi.org/10.1039/D1NJ01987B
    55. Caroline Berrou, Sébastien Prévost. Palladium‐Catalyzed C8‐Oxygenation of Naphthalene Derivatives: Direct Access to Naphtholactone Skeleton. Advanced Synthesis & Catalysis 2021, 363 (16) , 4091-4095. https://doi.org/10.1002/adsc.202100317
    56. Julia A. Brown, Alexandra L. Chaparro, Leah C. McCarthy, Sophia C. Moniodes, Erin E. Ostrowski, Maria E. Carroll. Iron tricarbonyl α-diimine complexes: Synthesis, characterization, and electronic structure based on X-ray crystal structures. Polyhedron 2021, 203 , 115168. https://doi.org/10.1016/j.poly.2021.115168
    57. Arup Mondal, Philipp Wedi, Manuel Gemmeren. The Non‐directed Distal C (sp 2 )– H Functionalization of Arenes. 2021, 191-219. https://doi.org/10.1002/9783527824137.ch7
    58. Daqian Zhu, Hui Peng, Yameng Sun, Zhouming Wu, Yun Wang, Bingling Luo, Tiantian Yu, Yumin Hu, Peng Huang, Shijun Wen. Modular metal-free catalytic radical annulation of cyclic diaryliodoniums to access π-extended arenes. Green Chemistry 2021, 23 (5) , 1972-1977. https://doi.org/10.1039/D0GC04183A
    59. Shunya Sakurai, Taichi Kano, Keiji Maruoka. Cu-Catalyzed O -alkylation of phenol derivatives with alkylsilyl peroxides. Chemical Communications 2021, 57 (1) , 81-84. https://doi.org/10.1039/D0CC07305A
    60. Manoj Kumar Ghosh, Nilendri Rout. Aryl‐Aryl Cross‐Coupling with Hypervalent Iodine Reagents: Aryl Group Transfer Reactions. ChemistrySelect 2020, 5 (43) , 13644-13655. https://doi.org/10.1002/slct.202003396
    61. Kai Wang, Jiahao Hou, Changjun Zhang, Ke Cheng, Renren Bai, Yuanyuan Xie. Palladium‐Catalyzed Picolinamide‐Directed Benzylic C( sp 3 )−H Chalcogenation with Diaryl Disulfides and Diphenyl Diselenide. Advanced Synthesis & Catalysis 2020, 362 (14) , 2947-2952. https://doi.org/10.1002/adsc.202000280
    62. Hideto Ito, Wataru Matsuoka, Yuuta Yano, Mari Shibata, Kenichiro Itami. Retraction: Annulative π-Extension (APEX) Reactions for Precise Synthesis of Polycyclic Aromatic Compounds. Journal of Synthetic Organic Chemistry, Japan 2020, 78 (7) , 671-682. https://doi.org/10.5059/yukigoseikyokaishi.78.671
    63. Jianxiao Li, Shaorong Yang, Wanqing Wu, Huanfeng Jiang. Recent developments in palladium-catalyzed C–S bond formation. Organic Chemistry Frontiers 2020, 7 (11) , 1395-1417. https://doi.org/10.1039/D0QO00377H
    64. Sébastien Prévost. Regioselective C−H Functionalization of Naphthalenes: Reactivity and Mechanistic Insights. ChemPlusChem 2020, 85 (3) , 476-486. https://doi.org/10.1002/cplu.202000005
    65. Hyung Yoon. Pd-Catalyzed Spirocyclization via C–H Activation and Benzyne/Alkyne Insertion. 2020, 141-212. https://doi.org/10.1007/978-3-030-54077-7_3
    66. Julian Garrec, Marie Cordier, Gilles Frison, Sébastien Prévost. Palladium‐Catalyzed C8‐Arylation of Naphthalenes through C−H Activation: A Combined Experimental and Computational Study. Chemistry – A European Journal 2019, 25 (63) , 14441-14446. https://doi.org/10.1002/chem.201903500
    67. Vikas Dwivedi, Deepti Kalsi, Basker Sundararaju. Electrochemical‐/Photoredox Aspects of Transition Metal‐Catalyzed Directed C−H Bond Activation. ChemCatChem 2019, 11 (21) , 5160-5187. https://doi.org/10.1002/cctc.201900680
    68. Jia‐Jia Lin, Jun Zhou, Panpan Wu, Chao Chen. CuO‐Catalyzed 1,3‐Addition of Diaryliodonium Triflates to Diazo Esters for the Stereoselective Synthesis of Triflate‐Substituted β‐Aryloxyl Acrylates. European Journal of Organic Chemistry 2019, 2019 (34) , 5963-5969. https://doi.org/10.1002/ejoc.201901017
    69. Huw M. L. Davies, Kuangbiao Liao. Dirhodium tetracarboxylates as catalysts for selective intermolecular C–H functionalization. Nature Reviews Chemistry 2019, 3 (6) , 347-360. https://doi.org/10.1038/s41570-019-0099-x
    70. Benjamin Large, Nicolas Gigant, Delphine Joseph, Gilles Clavier, Damien Prim. Site‐Selective Arylation of Naphthalenes: a Key Entry towards Extended Fluorenones and Phenanthridinones. European Journal of Organic Chemistry 2019, 2019 (8) , 1835-1841. https://doi.org/10.1002/ejoc.201900067
    71. Piret Villo, Berit Olofsson. Arylations Promoted by Hypervalent Iodine Reagents. 2018, 1-61. https://doi.org/10.1002/9780470682531.pat0950
    72. Kuangbiao Liao, Yun-Fang Yang, Yingzi Li, Jacob N. Sanders, K. N. Houk, Djamaladdin G. Musaev, Huw M. L. Davies. Design of catalysts for site-selective and enantioselective functionalization of non-activated primary C–H bonds. Nature Chemistry 2018, 10 (10) , 1048-1055. https://doi.org/10.1038/s41557-018-0087-7
    73. Philipp Wedi, Manuel van Gemmeren. Arene‐Limited Nondirected C−H Activation of Arenes. Angewandte Chemie International Edition 2018, 57 (40) , 13016-13027. https://doi.org/10.1002/anie.201804727
    74. Philipp Wedi, Manuel van Gemmeren. Die Aren‐limitierte nicht‐dirigierte C‐H‐Aktivierung von Aromaten. Angewandte Chemie 2018, 130 (40) , 13198-13209. https://doi.org/10.1002/ange.201804727
    75. Zhenlan Fang, Qiang Ju. Role of Defects in Catalysis. 2018, 341-378. https://doi.org/10.1002/9783527809097.ch11
    76. Jianxiao Li, Can Li, Lu Ouyang, Chunsheng Li, Shaorong Yang, Wanqing Wu, Huanfeng Jiang. Palladium‐Catalyzed Regioselective Three‐Component Cascade Bisthiolation of Terminal Alkynes. Advanced Synthesis & Catalysis 2018, 360 (6) , 1138-1150. https://doi.org/10.1002/adsc.201701417
    77. Richard C. Larock, Xiaoxia Zhang. Formation of Alkanes and Arenes by Coupling Reactions. 2018, 1-149. https://doi.org/10.1002/9781118662083.cot01-002
    78. Hiroyuki Kitano, Wataru Matsuoka, Hideto Ito, Kenichiro Itami. Annulative π-extension of indoles and pyrroles with diiodobiaryls by Pd catalysis: rapid synthesis of nitrogen-containing polycyclic aromatic compounds. Chemical Science 2018, 9 (38) , 7556-7561. https://doi.org/10.1039/C8SC02802H
    79. Hideto Ito, Kyohei Ozaki, Kenichiro Itami. Die anellierende Erweiterung von π-Systemen (APEX-Reaktion): ein rascher Zugang zu kondensierten Arenen, Heteroarenen und Nanographenen. Angewandte Chemie 2017, 129 (37) , 11296-11317. https://doi.org/10.1002/ange.201701058
    80. Hideto Ito, Kyohei Ozaki, Kenichiro Itami. Annulative π‐Extension (APEX): Rapid Access to Fused Arenes, Heteroarenes, and Nanographenes. Angewandte Chemie International Edition 2017, 56 (37) , 11144-11164. https://doi.org/10.1002/anie.201701058
    81. Jack Twilton, Chi Le, Patricia Zhang, Megan H. Shaw, Ryan W. Evans, David W. C. MacMillan. The merger of transition metal and photocatalysis. Nature Reviews Chemistry 2017, 1 (7) https://doi.org/10.1038/s41570-017-0052
    82. Tomohiro Hattori, Shun Ueda, Ryoya Takakura, Yoshinari Sawama, Yasunari Monguchi, Hironao Sajiki. Heterogeneous One‐Pot Carbonylation and Mizoroki–Heck Reaction in a Parallel Manner Following the Cleavage of Cinnamaldehyde Derivatives. Chemistry – A European Journal 2017, 23 (34) , 8196-8202. https://doi.org/10.1002/chem.201606048
    83. Yat‐Ming So, Ka‐Chun Au‐Yeung, Herman H. ‐Y. Sung, Ian D. Williams, Wa‐Hung Leung. Synthesis, Structure, and Reductive Elimination of Cationic Monoarylpalladium(IV) Complexes Supported by a Tripodal Oxygen Ligand. European Journal of Inorganic Chemistry 2017, 2017 (22) , 2928-2935. https://doi.org/10.1002/ejic.201700326
    84. Felipe Sousa e Silva, Anthony Tierno, Sarah Wengryniuk. Hypervalent Iodine Reagents in High Valent Transition Metal Chemistry. Molecules 2017, 22 (5) , 780. https://doi.org/10.3390/molecules22050780
    85. Szabolcs Kovács, Balázs L. Tóth, Gábor Borsik, Tamás Bihari, Nóra V. May, András Stirling, Zoltán Novák. Direct ortho ‐Trifluoroethylation of Aromatic Ureas by Palladium Catalyzed C‐H activation: A Missing Piece of Aromatic Substitutions. Advanced Synthesis & Catalysis 2017, 359 (3) , 527-532. https://doi.org/10.1002/adsc.201601136
    86. Lei Zhang, Yunpeng Wang, Liyao Zheng, Biao Guo, Ruimao Hua. Synthesis of fused polycyclic indoles via Cu(II)-catalyzed intramolecular cyclization of N-(2-cyanophenyl)indoles in the presence of diaryliodonium salts. Tetrahedron 2017, 73 (4) , 395-402. https://doi.org/10.1016/j.tet.2016.12.022
    87. Fu-Min Chen, Dong-Dong Lu, Li-Qun Hu, Ju Huang, Feng-Shou Liu. Camphyl-based α-diimine palladium complexes: highly efficient precatalysts for direct arylation of thiazoles in open-air. Organic & Biomolecular Chemistry 2017, 15 (27) , 5731-5736. https://doi.org/10.1039/C7OB00856B
    88. Tamao Ishida, Zhenzhong Zhang, Haruno Murayama, Makoto Tokunaga. Oxide-Supported Palladium and Gold Nanoparticles for Catalytic C-H Transformations. Journal of Synthetic Organic Chemistry, Japan 2017, 75 (11) , 1150-1161. https://doi.org/10.5059/yukigoseikyokaishi.75.1150
    89. Laure Théveau, Cédric Schneider, Corinne Fruit, Christophe Hoarau. Orthogonal Palladium‐Catalyzed Direct C−H Bond Arylation of Heteroaromatics with Aryl Halides. ChemCatChem 2016, 8 (20) , 3183-3194. https://doi.org/10.1002/cctc.201600489
    90. Xuesong Wang, Dayun Huang, Xingyong Wang, Xiaobao Zeng, Xinyan Wang, Yuefei Hu. Copper(II) triflate-catalyzed direct arylation for synthesis of biphenyls using diaryliodonium salts as arylating reagents. Tetrahedron Letters 2016, 57 (37) , 4235-4238. https://doi.org/10.1016/j.tetlet.2016.08.027
    91. Jonathan Latham, Jean-Marc Henry, Humera H. Sharif, Binuraj R. K. Menon, Sarah A. Shepherd, Michael F. Greaney, Jason Micklefield. Integrated catalysis opens new arylation pathways via regiodivergent enzymatic C–H activation. Nature Communications 2016, 7 (1) https://doi.org/10.1038/ncomms11873
    92. Ekaterina Bolbat, Ola F. Wendt. Ligand Control in Selective C–H Oxidative Functionalization Using Pd‐PEPPSI‐Type Complexes. European Journal of Organic Chemistry 2016, 2016 (20) , 3395-3400. https://doi.org/10.1002/ejoc.201600322
    93. Masahito Murai, Mayu Yanagawa, Masahiro Nakamura, Kazuhiko Takai. Palladium‐Catalyzed Direct Arylation of Azulene Based on Regioselective C−H Bond Activation. Asian Journal of Organic Chemistry 2016, 5 (5) , 629-635. https://doi.org/10.1002/ajoc.201600062
    94. Sabir Ahammed, Shiny Nandi, Debasish Kundu, Brindaban C. Ranu. One-pot Suzuki coupling of aromatic amines via visible light photocatalyzed metal free borylation using t-BuONO at room temperature. Tetrahedron Letters 2016, 57 (14) , 1551-1554. https://doi.org/10.1016/j.tetlet.2016.02.097
    95. Soumitra Agasti, Aniruddha Dey, Debabrata Maiti. Traceless directing group mediated branched selective alkenylation of unbiased arenes. Chemical Communications 2016, 52 (82) , 12191-12194. https://doi.org/10.1039/C6CC07032A
    96. H. M. D. Bandara, D. Jin, M. A. Mantell, K. D. Field, A. Wang, R. P. Narayanan, N. A. Deskins, M. H. Emmert. Non-directed aromatic C–H amination: catalytic and mechanistic studies enabled by Pd catalyst and reagent design. Catalysis Science & Technology 2016, 6 (14) , 5304-5310. https://doi.org/10.1039/C6CY00457A
    97. Jia-Sheng Ouyang, Yan-Fang Li, Dong-Sheng Shen, Zhuofeng Ke, Feng-Shou Liu. Bulky α-diimine palladium complexes: highly efficient for direct C–H bond arylation of heteroarenes under aerobic conditions. Dalton Transactions 2016, 45 (38) , 14919-14927. https://doi.org/10.1039/C6DT02544G
    98. Jiao Song, Wenbo Chen, Yunjie Zhao, Chenglong Li, Guang Liang, Lehao Huang. Palladium-catalyzed ortho C–H bond alkylation of benzylamides with α-bromo ketones. RSC Advances 2016, 6 (60) , 54984-54992. https://doi.org/10.1039/C6RA07450B
    99. Rukiya Matsidik, Alessandro Luzio, Sophie Hameury, Hartmut Komber, Christopher R. McNeill, Mario Caironi, Michael Sommer. Effects of PNDIT2 end groups on aggregation, thin film structure, alignment and electron transport in field-effect transistors. Journal of Materials Chemistry C 2016, 4 (43) , 10371-10380. https://doi.org/10.1039/C6TC03804B
    100. Dipannita Kalyani, Elodie E. Marlier. Reactivity and Selectivity in Transition Metal‐Catalyzed, Nondirected Arene Functionalizations. 2015, 675-713. https://doi.org/10.1002/9781118754887.ch24
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