Intramolecular C−H Amination Reactions:  Exploitation of the Rh₂(II)-Catalyzed Decomposition of Azidoacrylates

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14. Ian G. Powers, John M. Andjaba, Matthias Zeller, Christopher Uyeda. Catalytic C(sp2)–H Amination Reactions Using Dinickel Imides. Organometallics 2020, 39 (21) , 3794-3801. https://doi.org/10.1021/acs.organomet.0c00504
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16. Xiaofei Zhang, Peiyuan Zhu, Ruihong Zhang, Xiang Li, Tuanli Yao. Visible-Light-Induced Decarboxylative Cyclization of 2-Alkenylarylisocyanides with α-Oxocarboxylic Acids: Access to 2-Acylindoles. The Journal of Organic Chemistry 2020, 85 (15) , 9503-9513. https://doi.org/10.1021/acs.joc.0c00039
17. Yeongyu Hwang, Hoimin Jung, Euijae Lee, Dongwook Kim, Sukbok Chang. Quantitative Analysis on Two-Point Ligand Modulation of Iridium Catalysts for Chemodivergent C–H Amidation. Journal of the American Chemical Society 2020, 142 (19) , 8880-8889. https://doi.org/10.1021/jacs.0c02079
18. Amol Milind Garkhedkar, Babasaheb Sopan Gore, Wan-Ping Hu, Jeh-Jeng Wang. Lewis Acid Catalyzed Atom-Economic Synthesis of C2-Substituted Indoles from o-Amido Alkynols. Organic Letters 2020, 22 (9) , 3531-3536. https://doi.org/10.1021/acs.orglett.0c00971
19. Anuvab Das, Yu-Sheng Chen, Joseph H. Reibenspies, David C. Powers. Characterization of a Reactive Rh2 Nitrenoid by Crystalline Matrix Isolation. Journal of the American Chemical Society 2019, 141 (41) , 16232-16236. https://doi.org/10.1021/jacs.9b09064
20. Jin-Sheng Yu, Miguel Espinosa, Hidetoshi Noda, Masakatsu Shibasaki. Traceless Electrophilic Amination for the Synthesis of Unprotected Cyclic β-Amino Acids. Journal of the American Chemical Society 2019, 141 (26) , 10530-10537. https://doi.org/10.1021/jacs.9b05476
21. Kang Zhao, Rongrong Du, Bingyang Wang, Jianhua Liu, Chungu Xia, Lei Yang. RhCl3·3H2O-Catalyzed Regioselective C(sp2)–H Alkoxycarbonylation: Efficient Synthesis of Indole- and Pyrrole-2-carboxylic Acid Esters. ACS Catalysis 2019, 9 (6) , 5545-5551. https://doi.org/10.1021/acscatal.9b01193
22. Tao Zhang, Xunqing Dong, Hitesh B. Jalani, Jiaqi Zou, Guigen Li, Hongjian Lu. Iridium-Catalyzed C–H Amination/Cyclization for Medium to Large N-Heterocycle-Fused Dihydroquinazolinones. Organic Letters 2019, 21 (10) , 3706-3710. https://doi.org/10.1021/acs.orglett.9b01167
23. Jinghe Cen, Yaodan Wu, Jianxiao Li, Liangbin Huang, Wanqing Wu, Zhongzhi Zhu, Shaorong Yang, Huanfeng Jiang. Switchable Reactivity between Vinyl Azides and Terminal Alkyne by Nano Copper Catalysis. Organic Letters 2019, 21 (7) , 2090-2094. https://doi.org/10.1021/acs.orglett.9b00373
24. Long Ren, Guanglei Nan, Yongcheng Wang, Zhiyan Xiao. Carboxylic Acid-Promoted Single-Step Indole Construction from Simple Anilines and Ketones via Aerobic Cross-Dehydrogenative Coupling. The Journal of Organic Chemistry 2018, 83 (23) , 14472-14488. https://doi.org/10.1021/acs.joc.8b02180
25. Yi Wang, Zaixiang Fang, Xiaochuan Chen, Yuanhua Wang. Mild Dirhodium(II)-Catalyzed Chemo- and Regioselective Azidation of Arenes. Organic Letters 2018, 20 (18) , 5732-5736. https://doi.org/10.1021/acs.orglett.8b02446
26. A. V. G. Prasanthi, Samiyara Begum, Hemant Kumar Srivastava, Sandip Kumar Tiwari, Ritesh Singh. Iron-Catalyzed Arene C–H Amidation Using Functionalized Hydroxyl Amines at Room Temperature. ACS Catalysis 2018, 8 (9) , 8369-8375. https://doi.org/10.1021/acscatal.8b02939
27. Jinghe Cen, Jianxiao Li, Yu Zhang, Zhongzhi Zhu, Shaorong Yang, Huanfeng Jiang. Direct Assembly of 4-Substituted Quinolines with Vinyl Azides as a Dual Synthon via C═C and C–N Bond Cleavage. Organic Letters 2018, 20 (15) , 4434-4438. https://doi.org/10.1021/acs.orglett.8b01718
28. Peng Chen, Chu-Han Sun, Yu Wang, Ying Xue, Chen Chen, Mei-Hua Shen, Hua-Dong Xu. Intramolecular Schmidt Reaction of Vinyl Azides with Cyclic Ketones. Organic Letters 2018, 20 (6) , 1643-1646. https://doi.org/10.1021/acs.orglett.8b00395
29. Daniel J. Tindall, Christophe Werlé, Richard Goddard, Petra Philipps, Christophe Farès, and Alois Fürstner . Structure and Reactivity of Half-Sandwich Rh(+3) and Ir(+3) Carbene Complexes. Catalytic Metathesis of Azobenzene Derivatives. Journal of the American Chemical Society 2018, 140 (5) , 1884-1893. https://doi.org/10.1021/jacs.7b12673
30. Jun Zhang, Yun Hu, Haiyu Wang, Aixin Guo, Jianshe Kong, Rujian Ma, Tao Wu, Yi Wang, Lian-Sheng Li, Wanping Mai, Pingda Ren, and Xiaohu Deng . Regioselective Functionalization of 4-Methyl-1H-indole for Scalable Synthesis of 2-Cyano-5-formyl-4-methyl-1H-indole. Organic Process Research & Development 2018, 22 (1) , 97-102. https://doi.org/10.1021/acs.oprd.7b00370
31. Hirohito Hayashi, Atsushi Kaga, and Shunsuke Chiba . Application of Vinyl Azides in Chemical Synthesis: A Recent Update. The Journal of Organic Chemistry 2017, 82 (23) , 11981-11989. https://doi.org/10.1021/acs.joc.7b02455
32. Xiaotian Qi, Yingzi Li, Ruopeng Bai, and Yu Lan . Mechanism of Rhodium-Catalyzed C–H Functionalization: Advances in Theoretical Investigation. Accounts of Chemical Research 2017, 50 (11) , 2799-2808. https://doi.org/10.1021/acs.accounts.7b00400
33. Haichao Ma, Xiaoyan Zhang, Liangliang Chen, and Wei Yu . A Domino Azidation/C–H Amination Approach toward Trifluoromethyl Substituted Imidazoles. The Journal of Organic Chemistry 2017, 82 (22) , 11841-11847. https://doi.org/10.1021/acs.joc.7b01361
34. Huabin Wan, Jian Xu, Qian Liu, Hongmin Li, Yan Lu, Manabu Abe, and Xiaoqing Zeng . Contrasting Photolytic and Thermal Decomposition of Phenyl Azidoformate: The Curtius Rearrangement Versus Intramolecular C–H Amination. The Journal of Physical Chemistry A 2017, 121 (45) , 8604-8613. https://doi.org/10.1021/acs.jpca.7b07969
35. Wen-Long Lei, Tao Wang, Kai-Wen Feng, Li-Zhu Wu, and Qiang Liu . Visible-Light-Driven Synthesis of 4-Alkyl/Aryl-2-Aminothiazoles Promoted by In Situ Generated Copper Photocatalyst. ACS Catalysis 2017, 7 (11) , 7941-7945. https://doi.org/10.1021/acscatal.7b02818
36. Joshua J. Farndon, Xiaofeng Ma, and John F. Bower . Transition Metal Free C–N Bond Forming Dearomatizations and Aryl C–H Aminations by in Situ Release of a Hydroxylamine-Based Aminating Agent. Journal of the American Chemical Society 2017, 139 (40) , 14005-14008. https://doi.org/10.1021/jacs.7b07830
37. Sagar Arepally, Venkata Nagarjuna Babu, Manickam Bakthadoss, and Duddu S. Sharada . A Direct Cycloaminative Approach to Imidazole Derivatives via Dual C–H Functionalization. Organic Letters 2017, 19 (19) , 5014-5017. https://doi.org/10.1021/acs.orglett.7b01840
38. Yoonsu Park, Youyoung Kim, and Sukbok Chang . Transition Metal-Catalyzed C–H Amination: Scope, Mechanism, and Applications. Chemical Reviews 2017, 117 (13) , 9247-9301. https://doi.org/10.1021/acs.chemrev.6b00644
39. Tsz Lung Lam, Ken Chi-Hang Tso, Bei Cao, Chen Yang, Daqing Chen, Xiao-Yong Chang, Jie-Sheng Huang, and Chi-Ming Che . Tripodal S-Ligand Complexes of Copper(I) as Catalysts for Alkene Aziridination, Sulfide Sulfimidation, and C–H Amination. Inorganic Chemistry 2017, 56 (8) , 4253-4257. https://doi.org/10.1021/acs.inorgchem.7b00226
40. Jia Wang, Hai-Tao Zhu, Si Chen, Yu Xia, Dong-Po Jin, Yi-Feng Qiu, Ying-Xiu Li, and Yong-Min Liang . Electrophilic Cyclization of Aryl Propargylic Alcohols: Synthesis of Dihalogenated 6,9-Dihydropyrido[1,2-a]indoles via a Cascade Iodocyclization. The Journal of Organic Chemistry 2016, 81 (22) , 10975-10986. https://doi.org/10.1021/acs.joc.6b02013
41. Swastik Karmakar, Prasanta Das, Debjyoti Ray, Subhankar Ghosh, and Shital K. Chattopadhyay . Ag(I)-Catalyzed Domino Cyclization–Addition Sequence with Simultaneous Carbonyl and Alkyne Activation as a Route to 2,2′-Disubstituted Bisindolylarylmethanes. Organic Letters 2016, 18 (20) , 5200-5203. https://doi.org/10.1021/acs.orglett.6b02321
42. Chen Kong, Navendu Jana, Crystalann Jones, and Tom G. Driver . Control of the Chemoselectivity of Metal N-Aryl Nitrene Reactivity: C–H Bond Amination versus Electrocyclization. Journal of the American Chemical Society 2016, 138 (40) , 13271-13280. https://doi.org/10.1021/jacs.6b07026
43. Ritesh Singh, Kommu Nagesh, and Matam Parameshwar . Rhodium(II)-Catalyzed Undirected and Selective C(sp2)–H Amination en Route to Benzoxazolones. ACS Catalysis 2016, 6 (10) , 6520-6524. https://doi.org/10.1021/acscatal.6b02237
44. Yunfei Zhou and Xiaoguang Bao . DFT Study of Pd(0)-Promoted Intermolecular C–H Amination with O-Benzoyl Hydroxylamines. Organic Letters 2016, 18 (18) , 4506-4509. https://doi.org/10.1021/acs.orglett.6b02093
45. Shu-Wei Wu and Feng Liu . Synthesis of α-Fluoroketones from Vinyl Azides and Mechanism Interrogation. Organic Letters 2016, 18 (15) , 3642-3645. https://doi.org/10.1021/acs.orglett.6b01691
46. Bijaya Kumar Singh, Arghya Polley, and Ranjan Jana . Copper(II)-Mediated Intermolecular C(sp2)–H Amination of Benzamides with Electron-Rich Anilines. The Journal of Organic Chemistry 2016, 81 (10) , 4295-4303. https://doi.org/10.1021/acs.joc.6b00659
47. Lin-Bao Zhang, Shou-Kun Zhang, Donghui Wei, Xinju Zhu, Xin-Qi Hao, Jian-Hang Su, Jun-Long Niu, and Mao-Ping Song . Cobalt(II)-Catalyzed C–H Amination of Arenes with Simple Alkylamines. Organic Letters 2016, 18 (6) , 1318-1321. https://doi.org/10.1021/acs.orglett.6b00241
48. Haichao Ma, Dianjun Li, and Wei Yu . Synthesis of Quinoxaline Derivatives via Tandem Oxidative Azidation/Cyclization Reaction of N-Arylenamines. Organic Letters 2016, 18 (4) , 868-871. https://doi.org/10.1021/acs.orglett.6b00148
49. Dmitry Borkin, Jonathan Pollock, Katarzyna Kempinska, Trupta Purohit, Xiaoqin Li, Bo Wen, Ting Zhao, Hongzhi Miao, Shirish Shukla, Miao He, Duxin Sun, Tomasz Cierpicki, and Jolanta Grembecka . Property Focused Structure-Based Optimization of Small Molecule Inhibitors of the Protein–Protein Interaction between Menin and Mixed Lineage Leukemia (MLL). Journal of Medicinal Chemistry 2016, 59 (3) , 892-913. https://doi.org/10.1021/acs.jmedchem.5b01305
50. Jiao Jiao, Kei Murakami, and Kenichiro Itami . Catalytic Methods for Aromatic C–H Amination: An Ideal Strategy for Nitrogen-Based Functional Molecules. ACS Catalysis 2016, 6 (2) , 610-633. https://doi.org/10.1021/acscatal.5b02417
51. Jarosław M. Granda, Jakub Grabowski, and Janusz Jurczak . Synthesis, Structure, and Complexation Properties of a C3-Symmetrical Triptycene-Based Anion Receptor: Selectivity for Dihydrogen Phosphate. Organic Letters 2015, 17 (23) , 5882-5885. https://doi.org/10.1021/acs.orglett.5b03066
52. Hai Xiao Siyang, Xiao Yue Ji, Xu Rui Wu, Xin Yan Wu, and Pei Nian Liu . Lewis Acid Catalyzed Tandem Polycyclization of Internal Alkynols and Vinyl Azides. Organic Letters 2015, 17 (21) , 5220-5223. https://doi.org/10.1021/acs.orglett.5b02556
53. Laura A. T. Cleghorn, Sébastien Albrecht, Laste Stojanovski, Frederick R. J. Simeons, Suzanne Norval, Robert Kime, Iain T. Collie, Manu De Rycker, Lorna Campbell, Irene Hallyburton, Julie A. Frearson, Paul G. Wyatt, Kevin D. Read, and Ian H. Gilbert . Discovery of Indoline-2-carboxamide Derivatives as a New Class of Brain-Penetrant Inhibitors of Trypanosoma brucei. Journal of Medicinal Chemistry 2015, 58 (19) , 7695-7706. https://doi.org/10.1021/acs.jmedchem.5b00596
54. Binhui Chen, Shanshan Guo, Xiao Guo, Guolin Zhang, and Yongping Yu . Selective Access to 4-Substituted 2-Aminothiazoles and 4-Substituted 5-Thiocyano-2-aminothiazoles from Vinyl Azides and Potassium Thiocyanate Switched by Palladium and Iron Catalysts. Organic Letters 2015, 17 (19) , 4698-4701. https://doi.org/10.1021/acs.orglett.5b02152
55. Xin Hong, Daniel A. Bercovici, Zhongyue Yang, Nezar Al-Bataineh, Ramya Srinivasan, Ram C. Dhakal, K. N. Houk, and Matthias Brewer . Mechanism and Dynamics of Intramolecular C–H Insertion Reactions of 1-Aza-2-azoniaallene Salts. Journal of the American Chemical Society 2015, 137 (28) , 9100-9107. https://doi.org/10.1021/jacs.5b04474
56. Feng-Cheng Jia, Cheng Xu, Zhi-Wen Zhou, Qun Cai, Deng-Kui Li, and An-Xin Wu . Consecutive Cycloaddition/SNAr/Reduction/Cyclization/Oxidation Sequences: A Copper-Catalyzed Multicomponent Synthesis of Fused N-Heterocycles. Organic Letters 2015, 17 (11) , 2820-2823. https://doi.org/10.1021/acs.orglett.5b01242
57. Monalisa Goswami, Volodymyr Lyaskovskyy, Sérgio R. Domingos, Wybren Jan Buma, Sander Woutersen, Oliver Troeppner, Ivana Ivanović-Burmazović, Hongjian Lu, Xin Cui, X. Peter Zhang, Edward J. Reijerse, Serena DeBeer, Matti M. van Schooneveld, Florian Felix Pfaff, Kallol Ray, and Bas de Bruin . Characterization of Porphyrin-Co(III)-‘Nitrene Radical’ Species Relevant in Catalytic Nitrene Transfer Reactions. Journal of the American Chemical Society 2015, 137 (16) , 5468-5479. https://doi.org/10.1021/jacs.5b01197
58. Kwangmin Shin, Hyunwoo Kim, and Sukbok Chang . Transition-Metal-Catalyzed C–N Bond Forming Reactions Using Organic Azides as the Nitrogen Source: A Journey for the Mild and Versatile C–H Amination. Accounts of Chemical Research 2015, 48 (4) , 1040-1052. https://doi.org/10.1021/acs.accounts.5b00020
59. Yin-Long Li, Jian Li, Ai-Lun Ma, Ya-Nan Huang, and Jun Deng . Metal-Free Synthesis of Indole via NIS-Mediated Cascade C–N Bond Formation/Aromatization. The Journal of Organic Chemistry 2015, 80 (8) , 3841-3851. https://doi.org/10.1021/acs.joc.5b00090
60. Qinghua Ren, Xiaoyan Shen, Jinyu Wan, and Jianhui Fang . Density Functional Theory Study of the Mechanisms of Iron-Catalyzed Intramolecular C–H Amination [1,2]-Shift Tandem Reactions of Aryl Azides. Organometallics 2015, 34 (6) , 1129-1136. https://doi.org/10.1021/acs.organomet.5b00087
61. Mikhail S. Novikov, Alexander F. Khlebnikov, Nikolai V. Rostovskii, Sergei Tcyrulnikov, Anna A. Suhanova, Kirill V. Zavyalov, and Dmitry S. Yufit . Pseudopericyclic 1,5- versus Pericyclic 1,4- and 1,6-Electrocyclization in Electron-Poor 4-Aryl-2-azabuta-1,3-dienes: Indole Synthesis from 2H-Azirines and Diazo Compounds. The Journal of Organic Chemistry 2015, 80 (1) , 18-29. https://doi.org/10.1021/jo501051n
62. Jiangling Peng, Zeqiang Xie, Ming Chen, Jian Wang, and Qiang Zhu . Copper-Catalyzed C(sp2)–H Amidation with Azides as Amino Sources. Organic Letters 2014, 16 (18) , 4702-4705. https://doi.org/10.1021/ol502010g
63. Vladimir T. Abaev, Anastasiya T. Plieva, Petrakis N. Chalikidi, Maxim G. Uchuskin, Igor V. Trushkov, and Alexander V. Butin . A Simple Route to Polysubstituted Indoles Exploiting Azide Induced Furan Ring Opening. Organic Letters 2014, 16 (16) , 4150-4153. https://doi.org/10.1021/ol5018504
64. Zhenhua Liu, Peiqiu Liao, and Xihe Bi . General Silver-Catalyzed Hydroazidation of Terminal Alkynes by Combining TMS-N3 and H2O: Synthesis of Vinyl Azides. Organic Letters 2014, 16 (14) , 3668-3671. https://doi.org/10.1021/ol501661k
65. Fei Zhou and Tom G. Driver . Efficient Synthesis of 3H-Indoles Enabled by the Lead-Mediated α-Arylation of β-Ketoesters or γ-Lactams Using Aryl Azides. Organic Letters 2014, 16 (11) , 2916-2919. https://doi.org/10.1021/ol5010615
66. Stefan G. Koenig, John W. Dankwardt, Yanbing Liu, Hang Zhao, and Surendra P. Singh . Copper-Catalyzed Synthesis of Indoles and Related Heterocycles in Renewable Solvents. ACS Sustainable Chemistry & Engineering 2014, 2 (6) , 1359-1363. https://doi.org/10.1021/sc5002098
67. Wenyan Hao, Yuanyuan Jiang, and Mingzhong Cai . Synthesis of Indolyl Imidazole Derivatives via Base-Promoted Tandem Reaction of N-[2-(1-Alkynyl)phenyl]carbodiimides with Isocyanides. The Journal of Organic Chemistry 2014, 79 (8) , 3634-3640. https://doi.org/10.1021/jo402552c
68. Leepakshi Khurana, Hamed I. Ali, Teresa Olszewska, Kwang H. Ahn, Aparna Damaraju, Debra A. Kendall, and Dai Lu . Optimization of Chemical Functionalities of Indole-2-carboxamides To Improve Allosteric Parameters for the Cannabinoid Receptor 1 (CB1). Journal of Medicinal Chemistry 2014, 57 (7) , 3040-3052. https://doi.org/10.1021/jm5000112
69. Maciej Krzeszewski, Bjarne Thorsted, Jonathan Brewer, and Daniel T. Gryko . Tetraaryl-, Pentaaryl-, and Hexaaryl-1,4-dihydropyrrolo[3,2-b]pyrroles: Synthesis and Optical Properties. The Journal of Organic Chemistry 2014, 79 (7) , 3119-3128. https://doi.org/10.1021/jo5002643
70. Navendu Jana, Quyen Nguyen, and Tom G. Driver . Development of a Suzuki Cross-Coupling Reaction between 2-Azidoarylboronic Pinacolate Esters and Vinyl Triflates To Enable the Synthesis of [2,3]-Fused Indole Heterocycles. The Journal of Organic Chemistry 2014, 79 (6) , 2781-2791. https://doi.org/10.1021/jo500252e
71. Sae Hume Park, Jaesung Kwak, Kwangmin Shin, Jaeyune Ryu, Yoonsu Park, and Sukbok Chang . Mechanistic Studies of the Rhodium-Catalyzed Direct C–H Amination Reaction Using Azides as the Nitrogen Source. Journal of the American Chemical Society 2014, 136 (6) , 2492-2502. https://doi.org/10.1021/ja411072a
72. Kandasamy Rajaguru, Rajendran Suresh, Arumugam Mariappan, Shanmugam Muthusubramanian, and Nattamai Bhuvanesh . Erbium Triflate Promoted Multicomponent Synthesis of Highly Substituted Imidazoles. Organic Letters 2014, 16 (3) , 744-747. https://doi.org/10.1021/ol403456b
73. Hang Zhao, Stefan G. Koenig, John W. Dankwardt, and Surendra P. Singh . Practical Nonazide Synthesis of a d-Amino Acid Oxidase Inhibitor via a Sequential Erlenmeyer–Plöchl Reaction and Ligand-Free Copper(I) Amination Protocol. Organic Process Research & Development 2014, 18 (1) , 198-204. https://doi.org/10.1021/op4001737
74. Huaiqing Zhao, Yaping Shang, and Weiping Su . Rhodium(III)-Catalyzed Intermolecular N-Chelator-Directed Aromatic C–H Amidation with Amides. Organic Letters 2013, 15 (19) , 5106-5109. https://doi.org/10.1021/ol4024776
75. Jaeyune Ryu, Jaesung Kwak, Kwangmin Shin, Donggun Lee, and Sukbok Chang . Ir(III)-Catalyzed Mild C–H Amidation of Arenes and Alkenes: An Efficient Usage of Acyl Azides as the Nitrogen Source. Journal of the American Chemical Society 2013, 135 (34) , 12861-12868. https://doi.org/10.1021/ja406383h
76. Chen Kong, Navendu Jana, and Tom G. Driver . Rh2(II)-Catalyzed Selective Aminomethylene Migration from Styryl Azides. Organic Letters 2013, 15 (4) , 824-827. https://doi.org/10.1021/ol400137q
77. B. V. Subba Reddy, M. Ramana Reddy, Y. Gopal Rao, J. S. Yadav, and B. Sridhar . Cu(OTf)2-Catalyzed Synthesis of 2,3-Disubstituted Indoles and 2,4,5-Trisubstituted Pyrroles from α-Diazoketones. Organic Letters 2013, 15 (3) , 464-467. https://doi.org/10.1021/ol303206w
78. Qi Zhang, Caihong Wu, Lixin Zhou, and Juan Li . Theoretical Studies on Intramolecular C–H Amination of Biaryl Azides Catalyzed by Four Different Late Transition Metals. Organometallics 2013, 32 (2) , 415-426. https://doi.org/10.1021/om300746z
79. Quyen Nguyen, Tuyen Nguyen, and Tom G. Driver . Iron(II) Bromide-Catalyzed Intramolecular C–H Bond Amination [1,2]-Shift Tandem Reactions of Aryl Azides. Journal of the American Chemical Society 2013, 135 (2) , 620-623. https://doi.org/10.1021/ja3113565
80. David E. Olson, D. Allen Roberts, and J. Du Bois . Synthesis of Differentially Substituted 1,2-Diamines through Advances in C–H Amination Technology. Organic Letters 2012, 14 (24) , 6174-6177. https://doi.org/10.1021/ol302895f
81. Hongli Bao and Uttam K. Tambar . Catalytic Enantioselective Allylic Amination of Unactivated Terminal Olefins via an Ene Reaction/[2,3]-Rearrangement. Journal of the American Chemical Society 2012, 134 (45) , 18495-18498. https://doi.org/10.1021/ja307851b
82. Ho-Fai Ip, Yat-Ming So, Herman H. Y. Sung, Ian D. Williams, and Wa-Hung Leung . Ruthenium-Mediated Double C–H Activation of Toluene with 1-Azidoadamantane. Organometallics 2012, 31 (19) , 7020-7023. https://doi.org/10.1021/om300499x
83. Camille Lescot, Benjamin Darses, Florence Collet, Pascal Retailleau, and Philippe Dauban . Intermolecular C–H Amination of Complex Molecules: Insights into the Factors Governing the Selectivity. The Journal of Organic Chemistry 2012, 77 (17) , 7232-7240. https://doi.org/10.1021/jo301563j
84. Gui-Rong Qu, Lei Liang, Hong-Ying Niu, Wei-Hao Rao, Hai-Ming Guo, and John S. Fossey . Copper-Catalyzed Synthesis of Purine-Fused Polycyclics. Organic Letters 2012, 14 (17) , 4494-4497. https://doi.org/10.1021/ol301848v
85. Ji Young Kim, Sae Hume Park, Jaeyune Ryu, Seung Hwan Cho, Seok Hwan Kim, and Sukbok Chang . Rhodium-Catalyzed Intermolecular Amidation of Arenes with Sulfonyl Azides via Chelation-Assisted C–H Bond Activation. Journal of the American Chemical Society 2012, 134 (22) , 9110-9113. https://doi.org/10.1021/ja303527m
86. Murali Mohan Guru and Tharmalingam Punniyamurthy . Copper(II)-Catalyzed Aerobic Oxidative Synthesis of Substituted 1,2,3- and 1,2,4-Triazoles from Bisarylhydrazones via C–H Functionalization/C–C/N–N/C–N Bonds Formation. The Journal of Organic Chemistry 2012, 77 (11) , 5063-5073. https://doi.org/10.1021/jo300592t
87. Quyen Nguyen, Ke Sun, and Tom G. Driver . Rh2(II)-Catalyzed Intramolecular Aliphatic C–H Bond Amination Reactions Using Aryl Azides as the N-Atom Source. Journal of the American Chemical Society 2012, 134 (17) , 7262-7265. https://doi.org/10.1021/ja301519q
88. Ayumi Takaoka, Marc-Etienne Moret, and Jonas C. Peters . A Ru(I) Metalloradical That Catalyzes Nitrene Coupling to Azoarenes from Arylazides. Journal of the American Chemical Society 2012, 134 (15) , 6695-6706. https://doi.org/10.1021/ja211603f
89. Francisco Velázquez, Srikanth Venkatraman, Charles A. Lesburg, José Duca, Stuart B. Rosenblum, Joseph A. Kozlowski, and F. George Njoroge . Synthesis of New 4,5-Dihydrofuranoindoles and Their Evaluation as HCV NS5B Polymerase Inhibitors. Organic Letters 2012, 14 (2) , 556-559. https://doi.org/10.1021/ol203177g
90. Bao Hu, Zhao Wang, Ning Ai, Jie Zheng, Xing-Hai Liu, Shang Shan, and Zhongwen Wang . Catalyst-Free Preparation of 1,2,4,5-Tetrasubstituted Imidazoles from a Novel Unexpected Domino Reaction of 2-Azido Acrylates and Nitrones. Organic Letters 2011, 13 (24) , 6362-6365. https://doi.org/10.1021/ol202650z
91. Yusuke Kobayashi, Mami Kuroda, Natsuki Toba, Mari Okada, Rie Tanaka, and Tetsutaro Kimachi . Highly Efficient Synthesis of Quinoxalinone-N-oxide via Tandem Nitrosation/Aerobic Oxidative C–N Bond Formation. Organic Letters 2011, 13 (23) , 6280-6283. https://doi.org/10.1021/ol202760c
92. Mark Edwin Harvey, Djamaladdin G. Musaev, and J. Du Bois . A Diruthenium Catalyst for Selective, Intramolecular Allylic C–H Amination: Reaction Development and Mechanistic Insight Gained through Experiment and Theory. Journal of the American Chemical Society 2011, 133 (43) , 17207-17216. https://doi.org/10.1021/ja203576p
93. Volodymyr Lyaskovskyy, Alma I. Olivos Suarez, Hongjian Lu, Huiling Jiang, X. Peter Zhang, and Bas de Bruin . Mechanism of Cobalt(II) Porphyrin-Catalyzed C–H Amination with Organic Azides: Radical Nature and H-Atom Abstraction Ability of the Key Cobalt(III)–Nitrene Intermediates. Journal of the American Chemical Society 2011, 133 (31) , 12264-12273. https://doi.org/10.1021/ja204800a
94. Huijun Dong, Regina T. Latka, and Tom G. Driver . Ruthenium-Catalyzed γ-Carbolinium Ion Formation from Aryl Azides; Synthesis of Dimebolin. Organic Letters 2011, 13 (10) , 2726-2729. https://doi.org/10.1021/ol2008268
95. Julien Bonnamour and Carsten Bolm . Iron(II) Triflate as a Catalyst for the Synthesis of Indoles by Intramolecular C−H Amination. Organic Letters 2011, 13 (8) , 2012-2014. https://doi.org/10.1021/ol2004066
96. Benjamin J. Stokes, Sheng Liu, and Tom G. Driver . Rh2(II)-Catalyzed Nitro-Group Migration Reactions: Selective Synthesis of 3-Nitroindoles from β-Nitro Styryl Azides. Journal of the American Chemical Society 2011, 133 (13) , 4702-4705. https://doi.org/10.1021/ja111060q
97. Charles S. Yeung and Vy M. Dong . Catalytic Dehydrogenative Cross-Coupling: Forming Carbon−Carbon Bonds by Oxidizing Two Carbon−Hydrogen Bonds. Chemical Reviews 2011, 111 (3) , 1215-1292. https://doi.org/10.1021/cr100280d
98. Andrew DeAngelis, Valerie W. Shurtleff, Olga Dmitrenko, and Joseph M. Fox . Rhodium(II)-Catalyzed Enantioselective C−H Functionalization of Indoles. Journal of the American Chemical Society 2011, 133 (6) , 1650-1653. https://doi.org/10.1021/ja1093309
99. Deng Hong, Zhengbo Chen, Xufeng Lin, and Yanguang Wang. Synthesis of Substituted Indoles from 2-Azidoacrylates and ortho-Silyl Aryltriflates. Organic Letters 2010, 12 (20) , 4608-4611. https://doi.org/10.1021/ol101934v
100. Samaresh Jana, Mack D. Clements, Barry K. Sharp and Nan Zheng. Fe(II)-Catalyzed Amination of Aromatic C−H Bonds via Ring Opening of 2H-Azirines: Synthesis of 2,3-Disubstituted Indoles. Organic Letters 2010, 12 (17) , 3736-3739. https://doi.org/10.1021/ol101130e