Double allylic defluorinative alkylation of 1,1-bisnucleophiles with (trifluoromethyl)alkenes: construction of all-carbon quaternary centers

被引：44

作者：

Cai, Yingying ^{[1
]}

Zeng, Hao ^{[1
]}

Zhu, Chuanle ^{[1
]}

Liu, Chi ^{[1
]}

Liu, Guangying ^{[1
]}

Jiang, Huanfeng ^{[1
]}

机构：

[1] South China Univ Technol, Sch Chem & Chem Engn, Key Lab Funct Mol Engn Guangdong Prov, Guangzhou 510610, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2020年 / 7卷 / 10期

基金：

中国国家自然科学基金;

关键词：

F BOND ACTIVATION; GEM-DIFLUOROALKENES; DIAZO-COMPOUNDS; FLUORINE; SUBSTITUTION; NITRILE; DIFLUOROOLEFINATION; PHARMACEUTICALS; CATALYSIS; TERTIARY;

D O I：

10.1039/d0qo00121j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A double allylic defluorinative alkylation reaction of 1,1-bisnucleophiles with (trifluoromethyl)alkenes is reported that occurs via the exclusively regioselective S(N)2 reaction. Various aliphatic nitriles, esters, and indolin-2-one derivatives could serve as 1,1-bisnucleophiles, delivering diverse attractive symmetric gem-difluoroalkene substituted products in high yields via the construction of all-carbon quaternary centers. Interestingly, the chemoselective SNV reaction between gem-difluoroalkenes and nucleophiles is completely inhibited. The nitrile group might help to stabilize the alpha-carbanion intermediates.

引用

页码：1260 / 1265

页数：6

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