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Visible‐Light‐Driven N‐Heterocyclic Carbene Catalyzed γ‐ and ϵ ‐Alkylation with Alkyl Radicals
Author(s) -
Dai Lei,
Xia ZiHao,
Gao YuanYuan,
Gao ZhongHua,
Ye Song
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201909017
Subject(s) - alkylation , carbene , alkyl , chemistry , catalysis , vicinal , radical , halide , photoredox catalysis , organic chemistry , combinatorial chemistry , photocatalysis
Abstract The merging of photoredox catalysis and N‐heterocyclic carbene (NHC) catalysis for γ‐ and ϵ‐alkylation of enals with alkyl radicals was developed. The alkylation reaction of γ‐oxidized enals with alkyl halides worked well for the synthesis γ‐multisubstituted‐α,β‐unsaturated esters, including those with challenging vicinal all‐carbon quaternary centers. The synthesis of ϵ‐multisubstituted‐α,β‐γ,δ‐diunsaturated esters by an unprecedented NHC‐catalyzed ϵ‐functionalization was also established.