硼鎓-瓦格纳-梅尔外因重排介导的烯烃亲电氟化反应.β-二氟烷基硼酸酯的合成途径
Electrophilic Fluorination of Alkenes via Bora-Wagner-Meerwein Rearrangement. Access to β-Difluoroalkyl Boronates.
机构信息
Department of Organic Chemistry, Stockholm University, Sweden.
出版信息
Angew Chem Int Ed Engl. 2021 Dec 6;60(50):26327-26331. doi: 10.1002/anie.202109461. Epub 2021 Nov 10.
Abstract
The electrophilic fluorination of geminal alkyl substituted vinyl-Bmida derivatives proceeds via bora-Wagner-Meerwein rearrangement. According to DFT modelling studies this rearrangement occurs with a low activation barrier via a bora-cyclopropane shaped TS. The Bmida group has a larger migration aptitude than the alkyl moiety in the Wagner-Meerwein rearrangement of the presented electrophilic fluorination reactions.
摘要
偕二烷基取代的乙烯基硼酰胺衍生物的亲电氟化反应通过硼瓦格纳-梅尔魏因重排进行。根据 DFT 模型研究，该重排通过硼环丙烷形状的 TS 以低活化能垒进行。在呈现的亲电氟化反应的瓦格纳-梅尔魏因重排中，Bmida 基团比烷基部分具有更大的迁移倾向。
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