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Cyclic Iodine Reagents Enable Allylic Alcohols for Alkyl Boronate Addition/Rearrangement by Photoredox Catalysis
Author(s) -
Liu Mingshang,
Huang Hanchu,
Chen Yiyun
Publication year - 2018
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201800461
Subject(s) - chemistry , allylic rearrangement , reagent , alkyl , catalysis , alcohol , pinacol , organic chemistry , combinatorial chemistry , olefin fiber , photoredox catalysis , iodine , organic synthesis , medicinal chemistry , photocatalysis
All‐carbon quaternary centers are prevalent in bioactive small molecules. However, their efficient construction remains a formidable synthetic challenge. Here we report cyclic iodine(III) reagents enable the synthesis of cyclopentanones, cyclohexanones, and dihydrofuranones bearing α‐quaternary centers by photoredox catalysis. The reaction proceeds by the formation of the novel cyclic iodine(III) reagent‐allylic alcohol complex, which enables the first alkyl boronate addition and semi‐pinacol rearrangement of allylic alcohols with dual alcohol and olefin activation. The reaction is suitable for gram scale synthesis and is transformable to alcohols, olefins, oximes, and lactones with an α‐quaternary center in one step.