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
收藏
页码：1260 / 1265
页数：6
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