Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

You’ve supercharged your research process with ACS and Mendeley!

STEP 1:
Click to create an ACS ID

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

MENDELEY PAIRING EXPIRED
Your Mendeley pairing has expired. Please reconnect
ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

Figure 1Loading Img

Pd(II)-Catalyzed Amination of C−H Bonds Using Single-Electron or Two-electron Oxidants

View Author Information
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037
Cite this: J. Am. Chem. Soc. 2009, 131, 31, 10806–10807
Publication Date (Web):July 16, 2009
https://doi.org/10.1021/ja904709b
Copyright © 2009 American Chemical Society

    Article Views

    16773

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Other access options
    Supporting Info (1)»

    Abstract

    Abstract Image

    Pd(II)-catalyzed intramolecular amination of arenes is developed using either a one- or two-electron oxidant. The reaction protocol tolerates a wide range of deactivating groups including acetyl, cyano, and nitro groups. This catalytic reaction allows expedient syntheses of broadly useful substituted indolines or indoles.

    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. You can change your affiliated institution below.

    Supporting Information

    ARTICLE SECTIONS
    Jump To

    Experimental procedure and characterization of all new compounds. This material is available free of charge via the Internet at http://pubs.acs.org.

    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

    This article is cited by 399 publications.

    1. Srinivasarao Yaragorla, Tabassum Khan, Jazeel Raoof. Cu-Catalyzed Oxidative C(sp2)–H Cycloetherification of o-Alkenyl Arenols for the Preparation of Fused Furans. The Journal of Organic Chemistry 2024, 89 (1) , 34-43. https://doi.org/10.1021/acs.joc.3c01251
    2. Sheba Ann Babu, Sunil Varughese, Jomon Mathew, Jubi John. Discovery of Oxygen Induced Chemoselectivity in Pd-Catalyzed C–H Functionalization: Cross-Dehydrogenative Coupling vs C–H Amination. The Journal of Organic Chemistry 2023, 88 (14) , 9877-9892. https://doi.org/10.1021/acs.joc.3c00651
    3. Yangyang Wang, Xiaobo Xu, Binghan Pang, Liqiang Hao, Gaorong Wu, Yafei Ji. Ligand-Enabled Sequential C(sp3)–H and C(sp2)–H Diolefination Reaction via Palladium Catalyst. Organic Letters 2022, 24 (37) , 6734-6739. https://doi.org/10.1021/acs.orglett.2c02502
    4. Priyambada Prusty, Subramanian Jambu, Masilamani Jeganmohan. Rh(III)-Catalyzed Selective Olefination of N-Carboxamide Indoles with Unactivated Olefins at Room Temperature via an Internal Oxidation. Organic Letters 2022, 24 (5) , 1121-1126. https://doi.org/10.1021/acs.orglett.1c03905
    5. Yuan Xue, Han Seul Park, Chao Jiang, Jin-Quan Yu. Palladium-Catalyzed β-C(sp3)–H Nitrooxylation of Ketones and Amides Using Practical Oxidants. ACS Catalysis 2021, 11 (22) , 14188-14193. https://doi.org/10.1021/acscatal.1c04188
    6. Qiyu Zhang, Xiong Xie, Jingjing Peng, Feiyang Chen, Jinyu Ma, Chunpu Li, Hong Liu, Dechuan Wang, Jiang Wang. Direct C4-Acetoxylation of Tryptophan and Tryptophan-Containing Peptides via Palladium(II)-Catalyzed C–H Activation. Organic Letters 2021, 23 (12) , 4699-4704. https://doi.org/10.1021/acs.orglett.1c01434
    7. Subramanian Jambu, Chikkabagilu Nagaraju Shambhavi, Masilamani Jeganmohan. Aerobic Oxidative C–H Olefination of Arylamides with Unactivated Olefins via a Rh(III)-Catalyzed C–H Activation. Organic Letters 2021, 23 (8) , 2964-2970. https://doi.org/10.1021/acs.orglett.1c00646
    8. Alen Bjelopetrović, Dajana Barišić, Zrinka Duvnjak, Ivan Džajić, Marina Juribašić Kulcsár, Ivan Halasz, Manuel Martínez, Ana Budimir, Darko Babić, Manda Ćurić. A Detailed Kinetico-Mechanistic Investigation on the Palladium C–H Bond Activation in Azobenzenes and Their Monopalladated Derivatives. Inorganic Chemistry 2020, 59 (23) , 17123-17133. https://doi.org/10.1021/acs.inorgchem.0c02418
    9. 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
    10. Yan-Qiao Chen, Yongwei Wu, Zhen Wang, Jennifer X. Qiao, Jin-Quan Yu. Transient Directing Group Enabled Pd-Catalyzed γ-C(sp3)–H Oxygenation of Alkyl Amines. ACS Catalysis 2020, 10 (10) , 5657-5662. https://doi.org/10.1021/acscatal.0c01310
    11. Álvaro Velasco-Rubio, Jesús A. Varela, Carlos Saá. Palladium-Catalyzed [5 + 2] Heteroannulation of Phenethylamides with 1,3-Dienes to Dopaminergic 3-Benzazepines. Organic Letters 2020, 22 (9) , 3591-3595. https://doi.org/10.1021/acs.orglett.0c01053
    12. Kaj M. van Vliet, Bas de Bruin. Dioxazolones: Stable Substrates for the Catalytic Transfer of Acyl Nitrenes. ACS Catalysis 2020, 10 (8) , 4751-4769. https://doi.org/10.1021/acscatal.0c00961
    13. Aurélien Jacquin-Labarre, Sébastien Coufourier, Rodolphe Tamion, Alexandra Le Foll, Vincent Levacher, Carlos Afonso, Vincent Gandon, Guillaume Journot, Jean-François Brière, Christophe Hoarau. Base-Assisted Intramolecular C–N Coupling Reaction from NH2-Bound Cyclopalladated l-Phenylalanine to Indoline-2-carboxylic Acid. Organometallics 2020, 39 (5) , 767-773. https://doi.org/10.1021/acs.organomet.0c00030
    14. Sk. Sheriff Shah, Maniklal Shee, Amit Kumar Singh, Amrita Paul, N. D. Pradeep Singh. Direct Oxygenation of C–H Bonds through Photoredox and Palladium Catalysis. The Journal of Organic Chemistry 2020, 85 (5) , 3426-3439. https://doi.org/10.1021/acs.joc.9b03197
    15. Tatyana V. Gryaznova, Kirill V. Kholin, Elizaveta O. Nikanshina, Vera V. Khrizanforova, Sofia O. Strekalova, Robert R. Fayzullin, Yulia H. Budnikova. Copper or Silver-Mediated Oxidative C(sp2)–H/N–H Cross-Coupling of Phthalimide and Heterocyclic Arenes: Access to N-Arylphthalimides. Organometallics 2019, 38 (19) , 3617-3628. https://doi.org/10.1021/acs.organomet.9b00443
    16. Zhong-Yuan Li, Hetti Handi Chaminda Lakmal, Xiaolin Qian, Zhenyu Zhu, Bruno Donnadieu, Sarah J. McClain, Xue Xu, Xin Cui. Ruthenium-Catalyzed Enantioselective C–H Functionalization: A Practical Access to Optically Active Indoline Derivatives. Journal of the American Chemical Society 2019, 141 (40) , 15730-15736. https://doi.org/10.1021/jacs.9b07251
    17. Andrew M. Romine, Kin S. Yang, Malkanthi K. Karunananda, Jason S. Chen, Keary M. Engle. Synthetic and Mechanistic Studies of a Versatile Heteroaryl Thioether Directing Group for Pd(II) Catalysis. ACS Catalysis 2019, 9 (9) , 7626-7640. https://doi.org/10.1021/acscatal.9b01471
    18. Xueliang Sun, Zhuo Wu, Weixin Qi, Xiaoming Ji, Cang Cheng, Yanghui Zhang. Synthesis of Indolines by Palladium-Catalyzed Intermolecular Amination of Unactivated C(sp3)–H Bonds. Organic Letters 2019, 21 (16) , 6508-6512. https://doi.org/10.1021/acs.orglett.9b02386
    19. Tong Xu, Dong Wang, Xiaofeng Tong. Pd(II)-Catalyzed Intramolecular Acetoxylative (3 + 2) Annulation of Propargylic Alcohol and Alkene: Polycyclic Oxa-heterocycle Synthesis and Mechanistic Insight. Organic Letters 2019, 21 (13) , 5368-5372. https://doi.org/10.1021/acs.orglett.9b02096
    20. Manuel Nappi, Matthew J. Gaunt. A Class of N–O-Type Oxidants To Access High-Valent Palladium Species. Organometallics 2019, 38 (1) , 143-148. https://doi.org/10.1021/acs.organomet.8b00712
    21. Wei Wei, Leilei Wang, Pengli Bao, Yun Shao, Huilan Yue, Daoshan Yang, Xiaobo Yang, Xiaohui Zhao, Hua Wang. Metal-Free C(sp2)–H/N–H Cross-Dehydrogenative Coupling of Quinoxalinones with Aliphatic Amines under Visible-Light Photoredox Catalysis. Organic Letters 2018, 20 (22) , 7125-7130. https://doi.org/10.1021/acs.orglett.8b03079
    22. Deng-Yuan Li, Shuo Liu, Shuang Chen, An Wang, Xiao-Ping Zhu, Pei-Nian Liu. Dual Role of Aryl Iodide in Cascade C–H Arylation/Amination: Arylation Reagent and Cocatalyst for C–N Formation. ACS Catalysis 2018, 8 (7) , 6407-6412. https://doi.org/10.1021/acscatal.8b01071
    23. Yam N. Timsina, B. Frank Gupton, Keith C. Ellis. Palladium-Catalyzed C–H Amination of C(sp2) and C(sp3)–H Bonds: Mechanism and Scope for N-Based Molecule Synthesis. ACS Catalysis 2018, 8 (7) , 5732-5776. https://doi.org/10.1021/acscatal.8b01168
    24. Manthena Chaitanya, Pazhamalai Anbarasan. Lewis Acid/Brønsted Acid Controlled Pd(II)-Catalyzed Chemodivergent Functionalization of C(sp2)–H Bonds with N-(Arylthio)i(a)mides. Organic Letters 2018, 20 (11) , 3362-3366. https://doi.org/10.1021/acs.orglett.8b01281
    25. Bing Lian, Lei Zhang, Shi-Jun Li, Lu-Lu Zhang, De-Cai Fang. PdIV Species Mediation in PdII-Catalyzed Direct Alkylation of Arenes with Oxiranes: A DFT Study. The Journal of Organic Chemistry 2018, 83 (6) , 3142-3148. https://doi.org/10.1021/acs.joc.7b03236
    26. 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
    27. Fan Yang, Jiaojiao Yu, Yun Liu, and Jin Zhu . Rhodium(III)-Catalyzed Oxadiazole-Directed Alkenyl C–H Activation for Synthetic Access to 2-Acylamino and 2-Amino Pyridines. The Journal of Organic Chemistry 2017, 82 (19) , 9978-9987. https://doi.org/10.1021/acs.joc.7b01303
    28. 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
    29. Jinguo Long, Xin Cao, Longzhi Zhu, Renhua Qiu, Chak-Tong Au, Shuang-Feng Yin, Takanori Iwasaki, and Nobuaki Kambe . Intramolecular, Site-Selective, Iodine-Mediated, Amination of Unactivated (sp3)C–H Bonds for the Synthesis of Indoline Derivatives. Organic Letters 2017, 19 (11) , 2793-2796. https://doi.org/10.1021/acs.orglett.7b00846
    30. Zhongyin Zhang, Jinxin Wang, Jian Li, Fan Yang, Guodu Liu, Wenjun Tang, Weiwei He, Jian-Jun Fu, Yun-Heng Shen, Ang Li, and Wei-Dong Zhang . Total Synthesis and Stereochemical Assignment of Delavatine A: Rh-Catalyzed Asymmetric Hydrogenation of Indene-Type Tetrasubstituted Olefins and Kinetic Resolution through Pd-Catalyzed Triflamide-Directed C–H Olefination. Journal of the American Chemical Society 2017, 139 (15) , 5558-5567. https://doi.org/10.1021/jacs.7b01718
    31. Qi-Liang Yang, Yi-Qian Li, Cong Ma, Ping Fang, Xiu-Jie Zhang, and Tian-Sheng Mei . Palladium-Catalyzed C(sp3)—H Oxygenation via Electrochemical Oxidation. Journal of the American Chemical Society 2017, 139 (8) , 3293-3298. https://doi.org/10.1021/jacs.7b01232
    32. Elikplim Abada, Peter Y. Zavalij, and Andrei N. Vedernikov . Reductive C(sp2)–N Elimination from Isolated Pd(IV) Amido Aryl Complexes Prepared Using H2O2 as Oxidant. Journal of the American Chemical Society 2017, 139 (2) , 643-646. https://doi.org/10.1021/jacs.6b12648
    33. Qiuping Ding, Shengqing Ye, Guolin Cheng, Peng Wang, Marcus E. Farmer, and Jin-Quan Yu . Ligand-Enabled meta-Selective C–H Arylation of Nosyl-Protected Phenethylamines, Benzylamines, and 2-Aryl Anilines. Journal of the American Chemical Society 2017, 139 (1) , 417-425. https://doi.org/10.1021/jacs.6b11097
    34. Naveen, Vadla Rajkumar, Srinivasarao Arulananda Babu, and Bojan Gopalakrishnan . Pd(II)-Catalyzed Bidentate Directing Group-Aided Chemoselective Acetoxylation of Remote ε-C(sp2)–H Bonds in Heteroaryl–Aryl-Based Biaryl Systems. The Journal of Organic Chemistry 2016, 81 (24) , 12197-12211. https://doi.org/10.1021/acs.joc.6b01933
    35. Arpan Banerjee, Parthasarathi Subramanian, and Krishna P. Kaliappan . Copper-Catalyzed Cascade Amination Route to N-Aryl Benzimidazoquinazolinones. The Journal of Organic Chemistry 2016, 81 (21) , 10424-10432. https://doi.org/10.1021/acs.joc.6b01287
    36. 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
    37. 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
    38. Kyle Clagg, Haiyun Hou, Adam B. Weinstein, David Russell, Shannon S. Stahl, and Stefan G. Koenig . Synthesis of Indole-2-carboxylate Derivatives via Palladium-Catalyzed Aerobic Amination of Aryl C–H Bonds. Organic Letters 2016, 18 (15) , 3586-3589. https://doi.org/10.1021/acs.orglett.6b01592
    39. Hiroshi Taneda, Kiyofumi Inamoto, and Yoshinori Kondo . Palladium-Catalyzed Highly Chemoselective Intramolecular C–H Aminocarbonylation of Phenethylamines to Six-Membered Benzolactams. Organic Letters 2016, 18 (11) , 2712-2715. https://doi.org/10.1021/acs.orglett.6b01171
    40. Hyunwoo Kim and Sukbok Chang . Transition-Metal-Mediated Direct C–H Amination of Hydrocarbons with Amine Reactants: The Most Desirable but Challenging C–N Bond-Formation Approach. ACS Catalysis 2016, 6 (4) , 2341-2351. https://doi.org/10.1021/acscatal.6b00293
    41. 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
    42. Huijie Qiao, Suyan Sun, Fan Yang, Yu Zhu, Weiguo Zhu, Yaxi Dong, Yusheng Wu, Xiangtao Kong, Ling Jiang, and Yangjie Wu . Copper(I)-Catalyzed Sulfonylation of 8-Aminoquinoline Amides with Sulfonyl Chlorides in Air. Organic Letters 2015, 17 (24) , 6086-6089. https://doi.org/10.1021/acs.orglett.5b03114
    43. Zhong-Yuan Li and Guan-Wu Wang . Palladium-Catalyzed Decarboxylative Ortho-Ethoxycarbonylation of O-Methyl Ketoximes and 2-Arylpyridines with Potassium Oxalate Monoester. Organic Letters 2015, 17 (19) , 4866-4869. https://doi.org/10.1021/acs.orglett.5b02422
    44. Zhong-Jian Cai, Chao Yang, Shun-Yi Wang, and Shun-Jun Ji . Palladium-Catalyzed Regioselective C–H Acylation of Biaryl-2-amines. The Journal of Organic Chemistry 2015, 80 (16) , 7928-7936. https://doi.org/10.1021/acs.joc.5b00962
    45. Patrick Cyr, Sophie Régnier, William S. Bechara, and André B. Charette . Rapid Access to 3-Aminoindazoles from Tertiary Amides. Organic Letters 2015, 17 (14) , 3386-3389. https://doi.org/10.1021/acs.orglett.5b00765
    46. Vincent N. G. Lindsay, Hélène M.-F. Viart, and Richmond Sarpong . Stereodivergent Intramolecular C(sp3)–H Functionalization of Azavinyl Carbenes: Synthesis of Saturated Heterocycles and Fused N-Heterotricycles. Journal of the American Chemical Society 2015, 137 (26) , 8368-8371. https://doi.org/10.1021/jacs.5b04295
    47. Stefan Ortgies and Alexander Breder . Selenium-Catalyzed Oxidative C(sp2)–H Amination of Alkenes Exemplified in the Expedient Synthesis of (Aza-)Indoles. Organic Letters 2015, 17 (11) , 2748-2751. https://doi.org/10.1021/acs.orglett.5b01156
    48. 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
    49. Kazutaka Takamatsu, Koji Hirano, Tetsuya Satoh, and Masahiro Miura . Synthesis of Indolines by Copper-Mediated Intramolecular Aromatic C–H Amination. The Journal of Organic Chemistry 2015, 80 (6) , 3242-3249. https://doi.org/10.1021/acs.joc.5b00307
    50. Rui Liu, Ze-Hai Lu, Xiao-Hui Hu, Jun-Li Li, and Xian-Jin Yang . Monocarboxylation and Intramolecular Coupling of Butenylated Arenes via Palladium-Catalyzed C–H Activation Process. Organic Letters 2015, 17 (6) , 1489-1492. https://doi.org/10.1021/acs.orglett.5b00376
    51. Alfonso García-Rubia, Eduardo Laga, Carlos Cativiela, Esteban P. Urriolabeitia, Ramón Gómez-Arrayás, and Juan C. Carretero . Pd-Catalyzed Directed ortho-C–H Alkenylation of Phenylalanine Derivatives. The Journal of Organic Chemistry 2015, 80 (6) , 3321-3331. https://doi.org/10.1021/jo502912m
    52. Gongyuan Zhao, Chunxia Chen, Yixia Yue, Yanhan Yu, and Jinsong Peng . Palladium(II)-Catalyzed Sequential C–H Arylation/Aerobic Oxidative C–H Amination: One-Pot Synthesis of Benzimidazole-Fused Phenanthridines from 2-Arylbenzimidazoles and Aryl Halides. The Journal of Organic Chemistry 2015, 80 (5) , 2827-2834. https://doi.org/10.1021/jo502632b
    53. Yu-Peng He, Chao Zhang, Mengyang Fan, Zhijie Wu, and Dawei Ma . Assembly of Indoline-2-carboxylate-Embodied Dipeptides via Pd-Catalyzed C(sp2)–H Bond Direct Functionalization. Organic Letters 2015, 17 (3) , 496-499. https://doi.org/10.1021/ol503514t
    54. Jiyun Sun, Daisy Zhang-Negrerie, Yunfei Du, and Kang Zhao . Synthesis of Chromeno[2,3-b]indol-11(6H)-one via PhI(OAc)2-Mediated Intramolecular Oxidative C(sp2)–N(H2) Bond Formation. The Journal of Organic Chemistry 2015, 80 (2) , 1200-1206. https://doi.org/10.1021/jo502276b
    55. Sichang Wang, Zhangqin Ni, Xin Huang, Jichao Wang, and Yuanjiang Pan . Copper-Catalyzed Direct Amidation of Heterocycles with N-Fluorobenzenesulfonimide. Organic Letters 2014, 16 (21) , 5648-5651. https://doi.org/10.1021/ol502724u
    56. Jian Han, Pei Liu, Chao Wang, Qian Wang, Jingyu Zhang, Yanwei Zhao, Daqing Shi, Zhibin Huang, and Yingsheng Zhao . Oxalyl Amide Assisted Palladium-Catalyzed Arylation of C(sp2)–H Bond at the δ Position. Organic Letters 2014, 16 (21) , 5682-5685. https://doi.org/10.1021/ol502745g
    57. Weiguang Yang, Jiuxi Chen, Xiaobo Huang, Jinchang Ding, Miaochang Liu, and Huayue Wu . Pd-Catalyzed Intramolecular Aerobic Oxidative C–H Amination of 2-Aryl-3-(arylamino)quinazolinones: Synthesis of Fluorescent Indazolo[3,2-b]quinazolinones. Organic Letters 2014, 16 (20) , 5418-5421. https://doi.org/10.1021/ol5026553
    58. Changqing Ye, Hui Zhu, and Zhiyuan Chen . Synthesis of Biaryl Tertiary Amines through Pd/Norbornene Joint Catalysis in a Remote C–H Amination/Suzuki Coupling Reaction. The Journal of Organic Chemistry 2014, 79 (18) , 8900-8905. https://doi.org/10.1021/jo501544h
    59. Qixue Qin and Shouyun Yu . Visible-Light-Promoted Redox Neutral C–H Amidation of Heteroarenes with Hydroxylamine Derivatives. Organic Letters 2014, 16 (13) , 3504-3507. https://doi.org/10.1021/ol501457s
    60. Qianqian Lu, Haizhu Yu, and Yao Fu . Mechanistic Study of Chemoselectivity in Ni-Catalyzed Coupling Reactions between Azoles and Aryl Carboxylates. Journal of the American Chemical Society 2014, 136 (23) , 8252-8260. https://doi.org/10.1021/ja4127455
    61. Hui Xu, Xixue Qiao, Shiping Yang, and Zengming Shen . Cu-Catalyzed Direct Amidation of Aromatic C–H Bonds: An Access to Arylamines. The Journal of Organic Chemistry 2014, 79 (10) , 4414-4422. https://doi.org/10.1021/jo5003592
    62. Laura J. Allen, Pablo J. Cabrera, Melissa Lee, and Melanie S. Sanford . N-Acyloxyphthalimides as Nitrogen Radical Precursors in the Visible Light Photocatalyzed Room Temperature C–H Amination of Arenes and Heteroarenes. Journal of the American Chemical Society 2014, 136 (15) , 5607-5610. https://doi.org/10.1021/ja501906x
    63. Qian-Ru Zhang, Ji-Rong Huang, Wei Zhang, and Lin Dong . Highly Functionalized Pyridines Synthesis from N-Sulfonyl Ketimines and Alkynes Using the N–S Bond as an Internal Oxidant. Organic Letters 2014, 16 (6) , 1684-1687. https://doi.org/10.1021/ol500345n
    64. Mónica H. Pérez-Temprano, Joy M. Racowski, Jeff W. Kampf, and Melanie S. Sanford . Competition between sp3-C–N vs sp3-C–F Reductive Elimination from PdIV Complexes. Journal of the American Chemical Society 2014, 136 (11) , 4097-4100. https://doi.org/10.1021/ja411433f
    65. 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
    66. Ming-Sheng Xie, Zhi-Liang Chu, Hong-Ying Niu, Gui-Rong Qu, and Hai-Ming Guo . A Copper-Catalyzed Domino Route toward Purine-Fused Tricyclic Derivatives. The Journal of Organic Chemistry 2014, 79 (3) , 1093-1099. https://doi.org/10.1021/jo4025489
    67. Tatsuaki Matsubara, Sobi Asako, Laurean Ilies, and Eiichi Nakamura . Synthesis of Anthranilic Acid Derivatives through Iron-Catalyzed Ortho Amination of Aromatic Carboxamides with N-Chloroamines. Journal of the American Chemical Society 2014, 136 (2) , 646-649. https://doi.org/10.1021/ja412521k
    68. Kui Wu, Zhoulong Fan, Yu Xue, Qizheng Yao, and Ao Zhang . Rh(III)-Catalyzed Intermolecular C–H Amination of 1-Aryl-1H-pyrazol-5(4H)-ones with Alkylamines. Organic Letters 2014, 16 (1) , 42-45. https://doi.org/10.1021/ol402965d
    69. Zhe Dong and Guangbin Dong . Ortho vs Ipso: Site-Selective Pd and Norbornene-Catalyzed Arene C–H Amination Using Aryl Halides. Journal of the American Chemical Society 2013, 135 (49) , 18350-18353. https://doi.org/10.1021/ja410823e
    70. Ling Chu, Xiao-Chen Wang, Curtis E. Moore, Arnold L. Rheingold, and Jin-Quan Yu . Pd-Catalyzed Enantioselective C–H Iodination: Asymmetric Synthesis of Chiral Diarylmethylamines. Journal of the American Chemical Society 2013, 135 (44) , 16344-16347. https://doi.org/10.1021/ja408864c
    71. Youngchul Park, Incheol Jeon, Seohyun Shin, Jiae Min, and Phil Ho Lee . Ruthenium-Catalyzed C–H Activation/Cyclization for the Synthesis of Phosphaisocoumarins. The Journal of Organic Chemistry 2013, 78 (20) , 10209-10220. https://doi.org/10.1021/jo401608v
    72. Ming Shang, Shao-Hang Zeng, Shang-Zheng Sun, Hui-Xiong Dai, and Jin-Quan Yu . Ru(II)-Catalyzed ortho-C–H Amination of Arenes and Heteroarenes at Room Temperature. Organic Letters 2013, 15 (20) , 5286-5289. https://doi.org/10.1021/ol402515s
    73. Hiroki Shigehisa, Eriko Nishi, Mayu Fujisawa, and Kou Hiroya . Cobalt-Catalyzed Hydrofluorination of Unactivated Olefins: A Radical Approach of Fluorine Transfer. Organic Letters 2013, 15 (20) , 5158-5161. https://doi.org/10.1021/ol402696h
    74. Dahan Eom, Yeonseok Jeong, Yea Rin Kim, Euichul Lee, Wonseok Choi, and Phil Ho Lee . Palladium-Catalyzed C(sp2 and sp3)–H Activation/C–O Bond Formation: Synthesis of Benzoxaphosphole 1- and 2-Oxides. Organic Letters 2013, 15 (20) , 5210-5213. https://doi.org/10.1021/ol402736v
    75. 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
    76. Qiang Liu, Qingjiang Li, Yongfan Ma, and Yanxing Jia . Direct Olefination at the C-4 Position of Tryptophan via C–H Activation: Application to Biomimetic Synthesis of Clavicipitic Acid. Organic Letters 2013, 15 (17) , 4528-4531. https://doi.org/10.1021/ol4020877
    77. 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
    78. Thomas A. Ramirez, Qian Wang, Yingguang Zhu, Huaiji Zheng, Xingao Peng, Richard G. Cornwall, and Yian Shi . Pd(0)-Catalyzed Sequential C–N Bond Formation via Allylic and Aromatic C–H Amination of α-Methylstyrenes with Diaziridinone. Organic Letters 2013, 15 (16) , 4210-4213. https://doi.org/10.1021/ol401935c
    79. Qing-Zhong Zheng, Peng Feng, Yu-Feng Liang, and Ning Jiao . Pd-Catalyzed Tandem C–H Azidation and N–N Bond Formation of Arylpyridines: A Direct Approach to Pyrido[1,2-b]indazoles. Organic Letters 2013, 15 (16) , 4262-4265. https://doi.org/10.1021/ol402060q
    80. Songjie Yu, Boshun Wan, and Xingwei Li . Rhodium(III)-Catalyzed C–H Activation and Amidation of Arenes Using N-Arenesulfonated Imides as Amidating Reagents. Organic Letters 2013, 15 (14) , 3706-3709. https://doi.org/10.1021/ol401569u
    81. Tian-Sheng Mei, Dasheng Leow, Han Xiao, Brian N. Laforteza, and Jin-Quan Yu . Synthesis of Indolines via Pd(II)-Catalyzed Amination of C–H Bonds Using PhI(OAc)2 as the Bystanding Oxidant. Organic Letters 2013, 15 (12) , 3058-3061. https://doi.org/10.1021/ol401246u
    82. Ruja Shrestha, Paramita Mukherjee, Yichen Tan, Zachary C. Litman, and John F. Hartwig . Sterically Controlled, Palladium-Catalyzed Intermolecular Amination of Arenes. Journal of the American Chemical Society 2013, 135 (23) , 8480-8483. https://doi.org/10.1021/ja4032677
    83. Xinglin Yang, Gang Shan, and Yu Rao . Synthesis of 2-Aminophenols and Heterocycles by Ru-Catalyzed C–H Mono- and Dihydroxylation. Organic Letters 2013, 15 (10) , 2334-2337. https://doi.org/10.1021/ol400437a
    84. Manas K. Ghorai and Y. Nanaji . Synthetic Route to Chiral Indolines via Ring-Opening/C–N Cyclization of Activated 2-Haloarylaziridines. The Journal of Organic Chemistry 2013, 78 (8) , 3867-3878. https://doi.org/10.1021/jo400287a
    85. Tanguy Saget, David Perez, and Nicolai Cramer . Synthesis of Functionalized Spiroindolines via Palladium-Catalyzed Methine C–H Arylation. Organic Letters 2013, 15 (6) , 1354-1357. https://doi.org/10.1021/ol400380y
    86. Peiming Gu, Jian Sun, Xiao-Yan Kang, Ming Yi, Xue-Qiang Li, Ping Xue, and Rui Li . A Formal Metal-Free N-Arylation via the Schmidt Reaction of Aromatic Aldehydes with an Azido Amine. Organic Letters 2013, 15 (5) , 1124-1127. https://doi.org/10.1021/ol400213f
    87. Xiu-Fen Cheng, Yan Li, Yi-Ming Su, Feng Yin, Jian-Yong Wang, Jie Sheng, Harit U. Vora, Xi-Sheng Wang, and Jin-Quan Yu . Pd(II)-Catalyzed Enantioselective C–H Activation/C–O Bond Formation: Synthesis of Chiral Benzofuranones. Journal of the American Chemical Society 2013, 135 (4) , 1236-1239. https://doi.org/10.1021/ja311259x
    88. Joan Albert, Xavier Ariza, Teresa Calvet, Mercé Font-Bardia, Jordi Garcia, Jaume Granell, Andrea Lamela, Blanca López, Manuel Martinez, Laura Ortega, Aleix Rodriguez, and David Santos . NH2 As a Directing Group: From the Cyclopalladation of Amino Esters to the Preparation of Benzolactams by Palladium(II)-Catalyzed Carbonylation of N-Unprotected Arylethylamines. Organometallics 2013, 32 (2) , 649-659. https://doi.org/10.1021/om301140t
    89. 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
    90. Marie-Laure Louillat and Frederic W. Patureau . Toward Polynuclear Ru–Cu Catalytic Dehydrogenative C–N Bond Formation, on the Reactivity of Carbazoles. Organic Letters 2013, 15 (1) , 164-167. https://doi.org/10.1021/ol303216u
    91. Irina P. Beletskaya and Andrei V. Cheprakov . The Complementary Competitors: Palladium and Copper in C–N Cross-Coupling Reactions. Organometallics 2012, 31 (22) , 7753-7808. https://doi.org/10.1021/om300683c
    92. Raul A. Leal, Danial R. Beaudry, Saeed K. Alzghari, and Richmond Sarpong . Synthesis of the Pentacyclic Skeleton of the Indole Alkaloid Arboflorine. Organic Letters 2012, 14 (20) , 5350-5353. https://doi.org/10.1021/ol302535r
    93. Jiantao Hu, Shi Chen, Yonghui Sun, Jing Yang, and Yu Rao . Synthesis of Tri- and Tetrasubstituted Pyrazoles via Ru(II) Catalysis: Intramolecular Aerobic Oxidative C–N Coupling. Organic Letters 2012, 14 (19) , 5030-5033. https://doi.org/10.1021/ol3022353
    94. Dmitrijs Lubriks, Igors Sokolovs, and Edgars Suna . Indirect C–H Azidation of Heterocycles via Copper-Catalyzed Regioselective Fragmentation of Unsymmetrical λ3-Iodanes. Journal of the American Chemical Society 2012, 134 (37) , 15436-15442. https://doi.org/10.1021/ja305574k
    95. Patrick S. Hanley, Seth L. Marquard, Thomas R. Cundari, and John F. Hartwig . Reductive Elimination of Alkylamines from Low-Valent, Alkylpalladium(II) Amido Complexes. Journal of the American Chemical Society 2012, 134 (37) , 15281-15284. https://doi.org/10.1021/ja307558x
    96. Xi-Ai Gao, Ru-Long Yan, Xian-Xue Wang, Hao Yan, Jian Li, Han Guo, and Guo-Sheng Huang . Pd(II)-Catalyzed Synthesis of Benzisoxazolones from Benzohydroxamic Acids via C–H Activation. The Journal of Organic Chemistry 2012, 77 (17) , 7700-7705. https://doi.org/10.1021/jo301180k
    97. 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
    98. 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
    99. Qing Xiao, Leiming Tian, Renchang Tan, Ying Xia, Di Qiu, Yan Zhang, and Jianbo Wang . Transition-Metal-Free Electrophilic Amination of Arylboroxines. Organic Letters 2012, 14 (16) , 4230-4233. https://doi.org/10.1021/ol301912a
    100. 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
    Load more citations