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Brønsted Acid‐Catalyzed Intramolecular α‐Arylation of Ketones with Phenolic Nucleophiles via Oxy‐Allyl Cation Intermediates
Author(s) -
Aota Yusuke,
Doko Yuki,
Kano Taichi,
Maruoka Keiji
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.202000169
Subject(s) - chemistry , nucleophile , umpolung , catalysis , brønsted–lowry acid–base theory , intramolecular force , medicinal chemistry , acid catalysis , nucleophilic addition , organic chemistry , organocatalysis , combinatorial chemistry , enantioselective synthesis
Nucleophilic addition to the oxy‐allyl cation intermediate has emerged as a promising methodology for functionalization of the α‐position of carbonyl compounds in an umpolung fashion. However, a structure of available carbon nucleophiles to trap the catalytically generated oxy‐allyl cation has been limited to highly nucleophilic ones. Herein, we report the Brønsted acid‐catalyzed α‐arylation of ketones employing less explored phenolic nucleophiles as carbon nucleophiles in the oxy‐allyl cation catalysis, affording ketones bearing an all carbon quaternary center at the α‐position.