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Visible‐Light‐Promoted Redox‐Neutral Cyclopropanation Reactions of α‐Substituted Vinylphosphonates and Other Michael Acceptors with Chloromethyl Silicate as Methylene Transfer Reagent
Author(s) -
Guo Ting,
Zhang Li,
Liu Xiaobo,
Fang Yewen,
Jin Xiaoping,
Yang Yi,
Li Yan,
Chen Bin,
Ouyang Minghui
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800761
Subject(s) - cyclopropanation , chemistry , methylene , reagent , michael reaction , alkene , ketone , photochemistry , organic chemistry , catalysis
The alkene cyclopropanation with chloromethyl silicate as a methylene transfer reagent has been accomplished via visible‐light‐mediated redox‐neutral catalysis. This method features broad functional group tolerance and mild conditions. In addition to α‐substituted vinylphosphonates, a range of Michael acceptors including α,β ‐unsaturated acrylate, ketone, amide and sulfone are suitable substrates for this photocatalytic cyclopropanation. An application of this protocol to the cyclopropanation of estrone derivative is also presented.