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Catalytic Electrophilic Alkylation of p ‐Quinones through a Redox Chain Reaction
Author(s) -
Xu XiaoLong,
Li Zhi
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201702885
Subject(s) - chemistry , hydroquinone , redox , electrophile , alkylation , catalysis , allylic rearrangement , lewis acids and bases , chain reaction , organic chemistry , photochemistry
Allylation and benzylation of p ‐quinones was achieved through an unusual redox chain reaction. Mechanistic studies suggest that the existence of trace hydroquinone initiates a redox chain reaction that consists of a Lewis acid catalyzed Friedel–Crafts alkylation and a subsequent redox equilibrium that regenerates hydroquinone. The electrophiles could be various allylic and benzylic esters. The addition of Hantzsch ester as an initiator improves the efficiency of the reaction.