Fluoride-Catalyzed Arylation of α-(Trifluoromethyl)styrene Derivatives with Silicon-Masked, Functionalized Aryl Pronucleophiles

被引：9
|
作者：
Rahman, Aliyaah J. M. [1 ]
Xu, Yannan [1 ]
Oestreich, Martin [1 ]
机构：
[1] Tech Univ Berlin, Inst Chem, D-10623 Berlin, Germany
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 30期
关键词：
F BOND ACTIVATION; GEM-DIFLUOROALKENES; CONCISE SYNTHESIS; ORGANOLITHIUM REAGENTS; TRIFLUOROMETHYL; ELIMINATION; GENERATION;
D O I：
10.1021/acs.orglett.3c02021
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An operationally simple transition-metal-free protocolfor thearylation of & alpha;-(trifluoromethyl)styrene derivatives with silicon-protectedfunctionalized aryl pronucleophiles is disclosed. Catalytic amountsof an anionic Lewis base such as fluoride trigger the release of thearyl nucleophile from N-aryl-N & PRIME;-silyldiazenes by desilylation along with denitrogenation. The thus-generatedcarbon nucleophiles engage in an allylic displacement with & alpha;-(trifluoromethyl)styreneelectrophiles to afford the corresponding geminal difluoroalkenes.
引用
收藏
页码：5636 / 5640
页数：5
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