Nickel-Catalyzed Reductive 1,2-Dialkynylation of Alkenes Bearing an 8-Aminoquinoline Directing Group

被引：31

作者：

Pan, Rui ^{[1
,2
]}

Shi, Cong ^{[1
,2
]}

Zhang, Dongquan ^{[1
,2
]}

Tian, Yang ^{[1
,2
]}

Guo, Songjin ^{[1
,2
]}

Yao, Hequan ^{[1
,2
]}

Lin, Aijun ^{[1
,2
]}

机构：

[1] China Pharmaceut Univ, SKLNM, Nanjing 210009, Jiangsu, Peoples R China

[2] China Pharmaceut Univ, Dept Med Chem, Sch Pharm, Nanjing 210009, Jiangsu, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 22期

基金：

中国国家自然科学基金;

关键词：

ENANTIOSELECTIVE SYNTHESIS; CASCADE CYCLIZATION; DIYNES; DICARBOFUNCTIONALIZATION; ALKYNYLATION; ALKYLATION; ACETYLENE; ALDEHYDES; BROMIDES; HALIDES;

D O I：

10.1021/acs.orglett.9b03147

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An unprecedented nickel-catalyzed reductive 1,2-dialkynylation of alkenes bearing an 8-aminoquinoline directing group has been developed. This method proceeded through a migratory insertion/reductive-coupling process under mild conditions with a wide substrate scope and good functional group tolerance, providing direct access to the synthetically flexible 1,5-diynes. Moreover, the 1,2-dialkynylation products could be further converted to borate-ester- or azide-functionalized 1,5-dienes, ditriazole, beta-diyne primary amide, and trisubstituted benzene.

引用

页码：8915 / 8920

页数：6

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