Hypervalent iodine-mediated β-difluoroalkylboron synthesis via an unusual 1,2-hydrogen shift enabled by boron substitution

被引:13
|
作者
Lv, Wen-Xin [1 ]
Li, Yin [1 ]
Cai, Yuan-Hong [1 ]
Tan, Dong-Hang [1 ]
Li, Zhan [1 ]
Li, Ji-Lin [1 ]
Li, Qingjiang [1 ]
Wang, Honggen [1 ,2 ]
机构
[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangdong Key Lab Chiral Mol & Drug Discovery, Guangzhou 510006, Peoples R China
[2] Guangxi Normal Univ, Sch Chem & Pharmaceut Sci, State Key Lab Chem & Mol Engn Med Resources, Guilin 541004, Peoples R China
基金
中国国家自然科学基金;
关键词
FLUORINATION; ACIDS; ARYL; DIFLUOROMETHYLATION; ACTIVATION; ALKENES; CARBON; MONO;
D O I
10.1039/d1sc06508d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
beta-Difluoroalkylborons, featuring functionally important CF2 moiety and synthetically valuable boron group, have great synthetic potential while remaining synthetically challenging. Herein we report a hypervalent iodine-mediated oxidative gem-difluorination strategy to realize the construction of gem-difluorinated alkylborons via an unusual 1,2-hydrogen migration event, in which the (N-methyliminodiacetyl) boronate (BMIDA) motif is responsible for the high regio- and chemoselectivity. The protocol provides facile access to a broad range of beta-difluoroalkylborons under rather mild conditions. The value of these products was demonstrated by further transformations of the boryl group into other valuable functional groups, providing a wide range of difluorine-containing molecules.
引用
收藏
页码:2981 / 2984
页数:4
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