Rhodium(III)-Catalyzed C-H Alkenylation/Directing Group Migration for the Regio- and Stereoselective Synthesis of Tetrasubstituted Alkenes

被引：41

作者：

Wu, Xiaowei ^{[1
,2
]}

Lu, Yangbin ^{[3
,4
]}

Qiao, Jin ^{[3
]}

Dai, Wenhao ^{[5
]}

Jia, Xiuwen ^{[1
]}

Ni, Hangcheng ^{[3
]}

Zhang, Xiaoning ^{[3
]}

Liu, Hong ^{[5
]}

Zhao, Fei ^{[1
,3
]}

机构：

[1] Chengdu Univ, Sichuan Ind Inst Antibiot, Antibiot Res & Reevaluat Key Lab Sichuan Prov, Chengdu 610052, Peoples R China

[2] Baylor Coll Med, Dept Pharmacol & Chem Biol, Houston, TX 77030 USA

[3] Chengdu Univ, Sichuan Ind Inst Antibiot, Jinhua Branch, Jinhua 321007, Zhejiang, Peoples R China

[4] Chinese Acad Sci, Shanghai Inst Mat Med, Key Lab Drug Res, Shanghai 201203, Peoples R China

[5] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 23期

基金：

中国国家自然科学基金;

关键词：

BOND FORMATION; N-PHENOXYACETAMIDES; EFFICIENT ACCESS; INTERNAL ALKYNES; DIRECT ADDITION; DIRECTING GROUP; INDOLES; OLEFINATION; HYDROARYLATION; ARENES;

D O I：

10.1021/acs.orglett.0c03077

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient Rh(III)-catalyzed C-H alkenylation/directing group migration cascade between indoles and alkynes for the assembly of tetrasubstituted alkenes is reported. The carbamoyl directing group migrates to the carbon of the alkene moiety of the products through rare Rh-catalyzed C-N bond cleavage after the C-H alkenylation step and thus acts as an internal amidation reagent. This protocol shows broad substrate scope, excellent regio/stereoselectivity, and good to excellent yields.

引用

页码：9163 / 9168

页数：6

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