Pd(II)-Catalyzed Amination of C−H Bonds Using Single-Electron or Two-electron OxidantsClick to copy article linkArticle link copied!
Abstract
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.
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(31)
, 21239-21244. https://doi.org/10.1021/jacs.4c07706
- 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
- 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)
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(37)
, 6734-6739. https://doi.org/10.1021/acs.orglett.2c02502
- 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
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(22)
, 14188-14193. https://doi.org/10.1021/acscatal.1c04188
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(12)
, 4699-4704. https://doi.org/10.1021/acs.orglett.1c01434
- 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
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(23)
, 17123-17133. https://doi.org/10.1021/acs.inorgchem.0c02418
- 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
- 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
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, 5657-5662. https://doi.org/10.1021/acscatal.0c01310
- 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
- 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
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(5)
, 767-773. https://doi.org/10.1021/acs.organomet.0c00030
- 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
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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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
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