C-H Activation-Based Traceless Synthesis via Electrophilic Removal of a Directing Group. Rhodium(III)-Catalyzed Entry into Indoles from N-Nitroso and α-Diazo-β-keto Compounds

被引：113

作者：

Wang, Jie ^{[1
]}

Wang, Mingyang ^{[1
]}

Chen, Kehao ^{[1
]}

Zha, Shanke ^{[1
]}

Song, Chao ^{[1
]}

Zhu, Jin ^{[1
]}

机构：

[1] Nanjing Natl Lab Microstruct, State Key Lab Coordinat Chem, Dept Polymer Sci & Engn, Sch Chem & Chem Engn, Nanjing 210093, Jiangsu, Peoples R China

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 05期

基金：

中国国家自然科学基金;

关键词：

RH(III)-CATALYZED SYNTHESIS; EFFICIENT SYNTHESIS; FORM ISOCOUMARINS; CARBOXYLIC-ACIDS; FACILE SYNTHESIS; BOND; FUNCTIONALIZATION; MILD; OLEFINATION; ALKYLATION;

D O I：

10.1021/acs.orglett.6b00310

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A distinct C-H activation-based traceless synthetic protocol-via electrophilic removal of a directing group is reported, complementing the currently exclusively used nucleophilic strategy. Rh(III)-catalyzed, N-nitrosodirected C-H activation allows the development of a traceless, atom- and step-economic, cascade approach for the synthesis of indole skeletons, starting from readily available N-nitroso and alpha-diazo-beta-keto compounds. Importantly, the cyclization/denitrosation reaction represents a hitherto unobserved reactivity pattern for the N-nitroso group.

引用

页码：1178 / 1181

页数：4

共 33 条

[1] Synthesis of 2,3-Disubstituted NH Indoles via Rhodium(III)-Catalyzed C-H Activation of Arylnitrones and Coupling with Diazo Compounds
Guo, Xin
Han, Jianwei
Liu, Yafeng
Qin, Mingda
Zhang, Xueguo
Chen, Baohua
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (21): : 11505 - 11511
[2] Rhodium(III)-Catalyzed Direct Cyanation of Aromatic C-H Bond to Form 2-(Alkylamino)benzonitriles Using N-Nitroso As Directing Group
Dong, Jiawei
Wu, Zhongjie
Liu, Zhengyi
Liu, Ping
Sun, Peipei
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (24): : 12588 - 12593
[3] Rhodium(iii)-catalyzed C-H activation/annulation of N-iminopyridinium ylides with alkynes and diazo compounds
Li, Xiang
Zhang, Ruihong
Qi, Yaoting
Zhao, Qing
Yao, Tuanli
ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (06): : 1190 - 1196
[4] Traceless Directing Strategy: Efficient Synthesis of N-Alkyl Indoles via Redox-Neutral C-H Activation
Wang, Chengming
Huang, Yong
ORGANIC LETTERS, 2013, 15 (20) : 5294 - 5297
[5] N-Oxide as a Traceless Oxidizing Directing Group: Mild Rhodium(III)-Catalyzed C-H Olefination for the Synthesis of ortho-Alkenylated Tertiary Anilines
Huang, Xiaolei
Huang, Jingsheng
Du, Chenglong
Zhang, Xingyi
Song, Feijie
You, Jingsong
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (49) : 12970 - 12974
[6] Synthesis of Naphthols by Rh(III)-Catalyzed Domino C-H Activation, Annulation, and Lactonization Using Sulfoxonium Ylide as a Traceless Directing Group
Hanchate, Vinayak
Kumar, Anil
Prabhu, Kandikere Ramaiah
ORGANIC LETTERS, 2019, 21 (20) : 8424 - 8428
[7] Rhodium(III)-Catalyzed ortho-Alkylation of Phenoxy Substrates with Diazo Compounds via C-H Activation: A Case of Decarboxylative Pyrimidine/Pyridine Migratory Cyclization Rather than Removal of Pyrimidine/Pyridine Directing Group
Ravi, Manjula
Allu, Srinivasarao
Swamy, K. C. Kumara
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (05): : 2355 - 2363
[8] Rh(III)-Catalyzed Synthesis of N-Unprotected Indoles from Imidamides and Diazo Ketoesters via C-H Activation and C-C/C-N Bond Cleavage
Qi, Zisong
Yu, Songjie
Li, Xingwei
ORGANIC LETTERS, 2016, 18 (04) : 700 - 703
[9] Synthesis of γ-Spirolactams via Rh(III)-Catalyzed C-H Activation/Directing Group Migration/Dearomatization/Spiroannulation of Indoles with 1,3-Enynes
Kumar, Sanjeev
Kanchupalli, Vinaykumar
ORGANIC LETTERS, 2024, 26 (42) : 8975 - 8981
[10] Regioselective Synthesis of 4-Substituted Indoles via C-H Activation: A Ruthenium Catalyzed Novel Directing Group Strategy
Lanke, Veeranjaneyulu
Prabhu, Kandikere Ramaiah
ORGANIC LETTERS, 2013, 15 (24) : 6262 - 6265

← 1 2 3 4 →