Chelation-assisted Rh(III)-catalyzed C2-selective oxidative C-H/C-H cross-coupling of indoles/pyrroles with heteroarenes

被引:114
作者
Qin, Xurong [1 ]
Liu, Hu [1 ]
Qin, Dekun [1 ]
Wu, Qian [1 ]
You, Jingsong [1 ]
Zhao, Dongbing [1 ]
Guo, Qiang [1 ]
Huang, Xiaolei [1 ]
Lan, Jingbo [1 ]
机构
[1] Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem,State Key Lab Biotherapy,West China Med, Chengdu 610064, Peoples R China
关键词
METALATION-DEPROTONATION MECHANISM; CATALYZED ORTHO-ARYLATION; BOND FORMATION; SIMPLE ARENES; UNACTIVATED ARENES; ACTIVATION; RHODIUM; ALKYNES; FUNCTIONALIZATION; DERIVATIVES;
D O I
10.1039/c3sc22241a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The chelation-assisted strategy has been endowed with some novel functions in the Rh(III)-catalyzed dehydrogenative coupling of indoles/pyrroles with heteroarenes. While the reaction conditions used are rather common, the strategy can close the homo-coupling pathway of each coupling partner, and dramatically extend substrate scope along with the exclusive indole or pyrrole C2-site selectivity. This is the first example describing that a catalytic system allows the oxidative C-H/C-H hetero-coupling not only between two electron-rich heteroarenes but also between electron-deficient and electron-rich heteroarenes, showing a further beneficial aspect of the Rh(III) catalysis.
引用
收藏
页码:1964 / 1969
页数:6
相关论文
共 60 条
[31]   Synthesis of Dragmacidin D via Direct C-H Couplings [J].
Mandal, Debashis ;
Yamaguchi, Atsushi D. ;
Yamaguchi, Junichiro ;
Itami, Kenichiro .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (49) :19660-19663
[32]   Copper(II)-Mediated Dehydrogenative Cross-Coupling of Heteroarenes [J].
Mao, Zhifeng ;
Wang, Zhe ;
Xu, Zhaoqing ;
Huang, Fei ;
Yu, Zhengkun ;
Wang, Rui .
ORGANIC LETTERS, 2012, 14 (15) :3854-3857
[33]   Synthesis of Fluorene Derivatives through Rhodium-Catalyzed Dehydrogenative Cyclization [J].
Morimoto, Keisuke ;
Itoh, Masaki ;
Hirano, Koji ;
Satoh, Tetsuya ;
Shibata, Yu ;
Tanaka, Ken ;
Miura, Masahiro .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (22) :5359-5362
[34]   Regioselective Synthesis of Indenols by Rhodium-Catalyzed C-H Activation and Carbocyclization of Aryl Ketones and Alkynes [J].
Muralirajan, Krishnamoorthy ;
Parthasarathy, Kanniyappan ;
Cheng, Chien-Hong .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (18) :4169-4172
[35]   Copper-Mediated and Copper-Catalyzed Cross-Coupling of Indoles and 1,3-Azoles: Double C-H Activation [J].
Nishino, Mayuko ;
Hirano, Koji ;
Satoh, Tetsuya ;
Miura, Masahiro .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (28) :6993-6997
[36]  
Patureau FW, 2012, ALDRICHIM ACTA, V45, P31
[37]   Diverse Strategies toward Indenol and Fulvene Derivatives: Rh-Catalyzed C-H Activation of Aryl Ketones Followed by Coupling with Internal Alkynes [J].
Patureau, Frederic W. ;
Besset, Tatiana ;
Kuhl, Nadine ;
Glorius, Frank .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (07) :2154-2156
[38]   Intramolecular Oxidative C-H Coupling for Medium-Ring Synthesis [J].
Pintori, Didier G. ;
Greaney, Michael F. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (05) :1209-1211
[39]   Regioselective Oxidative Arylation of Indoles Bearing N-Alkyl Protecting Groups: Dual C-H Functionalization via a Concerted Metalation-Deprotonation Mechanism [J].
Potavathri, Shathaverdhan ;
Pereira, Kyle C. ;
Gorelsky, Serge I. ;
Pike, Andrew ;
LeBris, Alexis P. ;
DeBoef, Brenton .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (41) :14676-14681
[40]   Copper(II)-Catalyzed Dehydrogenative Cross-Coupling between Two Azoles [J].
Qin, Xurong ;
Feng, Boya ;
Dong, Jiaxing ;
Li, Xiaoyu ;
Xue, Ying ;
Lan, Jingbo ;
You, Jingsong .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (17) :7677-7683