Rhodium(III)-Catalyzed [3+2] Annulation of 5-Aryl-2,3-dihydro-1H-pyrroles with Internal Alkynes through C(sp2)-H/Alkene Functionalization

被引：82

作者：

Zhou, Ming-Bo ^{[1
]}

Pi, Rui ^{[1
]}

Hu, Ming ^{[1
]}

Yang, Yuan ^{[1
]}

Song, Ren-Jie ^{[1
]}

Xia, Yuanzhi ^{[3
]}

Li, Jin-Heng ^{[1
,2
]}

机构：

[1] Hunan Univ, Coll Chem & Chem Engn, State Key Lab Chemo Biosensing & Chemometr, Changsha 410082, Hunan, Peoples R China

[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

[3] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 42期

关键词：

alkynes; annulation; heterocycles; rhodium; spiro compounds; H BOND ACTIVATION; AROMATIC KETIMINES; C-C; (-)-CEPHALOTAXINE; CARBOCYCLIZATION; HETEROCYCLES; DERIVATIVES; PHASE;

D O I：

10.1002/anie.201407175

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This study describes a new rhodium(III)-catalyzed [3+2] annulation of 5-aryl-2,3-dihydro-1H-pyrroles with internal alkynes using a Cu(OAc)(2) oxidant for building a spirocyclic ring system, which includes the functionalization of an aryl C(sp(2))H bond and addition/protonolysis of an alkene CC bond. This method is applicable to a wide range of 5-aryl-2,3-dihydro-1H-pyrroles and internal alkynes, and results in the assembly of the spiro[indene-1,2-pyrrolidine] architectures in good yields with excellent regioselectivities.

引用

页码：11338 / 11341

页数：4

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