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Bromomethyl Silicate: A Robust Methylene Transfer Reagent for Radical‐Polar Crossover Cyclopropanation of Alkenes
Author(s) -
Luo Wenping,
Fang Yewen,
Zhang Li,
Xu Tianhang,
Liu Yongjun,
Li Yan,
Jin Xiaoping,
Bao Jiakan,
Wu Xiaodong,
Zhang Zongyong
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000134
Subject(s) - cyclopropanation , chemistry , methylene , reagent , intramolecular force , aryl , organic chemistry , catalysis , alkyl
A general protocol for visible‐light‐induced cyclopropanation of alkenes was developed with bromomethyl silicate as a methylene transfer reagent, offering a robust tool for accessing highly valuable cyclopropanes. In addition to α‐aryl or methyl‐substituted Michael acceptors and styrene derivatives, the unactivated 1,1‐dialkyl ethylenes were also shown to be viable substrates. Apart from realizing the cyclopropanation of terminal alkenes, the methyl transfer reaction has been further demonstrated to be amenable to the internal olefins. The photocatalytic cyclopropanation of 1,3‐bis(1‐arylethenyl)benzenes was also achieved, giving polycyclopropane derivatives in excellent yields. With late‐stage cyclopropanation as the key strategy, the synthetic utility of this transformation was also demonstrated by the total synthesis of LG100268.