Rhodium(III)-Catalyzed Transannulation of Cyclopropenes with N-Phenoxyacetamides through C-H Activation

被引：176

作者：

Zhang, Hang ^{[1
,2
]}

Wang, Kang ^{[1
,2
]}

Wang, Bo ^{[1
,2
]}

Yi, Heng ^{[1
,2
]}

Hu, Fangdong ^{[1
,2
]}

Li, Changkun ^{[1
,2
]}

Zhang, Yan ^{[1
,2
]}

Wang, Jianbo ^{[1
,2
,3
]}

机构：

[1] Peking Univ, BNLMS, Coll Chem, Beijing 100871, Peoples R China

[2] Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing 100871, Peoples R China

[3] Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 48期

关键词：

carbenes; C-H activation; heterocycles; small ring compounds; rhodium; REGIOSELECTIVE SYNTHESIS; CATALYZED REARRANGEMENT; BOND ACTIVATION; ANNULATION; ALKYNES; ARYL; 2H-CHROMENES; METATHESIS; AMIDATION; OLEFINS;

D O I：

10.1002/anie.201408555

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient rhodium(III)-catalyzed synthesis of 2H-chromene from N-phenoxyacetamides and cyclopropenes has been developed. The reaction represents the first example of using cyclopropenes as a three-carbon unit in rhodium(III)-catalyzed C(sp(2))-H activations.

引用

页码：13234 / 13238

页数：5

共 69 条

[1] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope
Ackermann, Lutz
[J]. CHEMICAL REVIEWS, 2011, 111 (03) : 1315 - 1345
[2] [Anonymous], 2012, ANGEW CHE, DOI DOI 10.1002/ANGE.201201273
[3] [Anonymous], 2014, Angew. Chem, DOI DOI 10.1002/ANGE.201309650
[4] [Anonymous], 2012, Angew. Chem
[5] [Anonymous], 2012, ANGEW CHEM
[6] Archambeau A., 2012, ANGEW CHEM, V124, P11708
[7] Highly Efficient Stereoselective Catalytic C(sp3)?H Insertions with Donor Rhodium Carbenoids Generated from Cyclopropenes
Archambeau, Alexis
Miege, Frederic
Meyer, Christophe
Cossy, Janine
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (46) : 11540 - 11544
[8] Rh-Catalyzed Intermolecular Carbenoid Functionalization of Aromatic C-H Bonds by α-Diazomalonates
Chan, Wai-Wing
Lo, Siu-Fung
Zhou, Zhongyuan
Yu, Wing-Yiu
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) : 13565 - 13568
[9] Direct palladium-catalyzed arylation of cyclopropenes
Chuprakov, S
Rubin, M
Gevorgyan, V
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (11) : 3714 - 3715
[10] Regiodivergent metal-catalyzed rearrangement of 3-iminocyclopropenes into N-fused heterocycles
Chuprakov, Stepan
Gevorgyan, Vladimir
[J]. ORGANIC LETTERS, 2007, 9 (22) : 4463 - 4466

← 1 2 3 4 5 6 7 →