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Efficient Coupling Reaction of Quinone Monoacetal with Phenols Leading to Phenol Biaryls
Author(s) -
Kamitanaka Tohru,
Morimoto Koji,
Tsuboshima Kohei,
Koseki Daichi,
Takamuro Hitoho,
Dohi Toshifumi,
Kita Yasuyuki
Publication year - 2016
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.201608013
Subject(s) - phenols , phenol , steric effects , chemistry , quinone , catalysis , organic chemistry , reaction conditions , coupling reaction , transformation (genetics) , combinatorial chemistry , biochemistry , gene
A simple and efficient synthesis of phenol biaryls by the cross‐couplings of quinone monoacetals (QMAs) and phenols is reported. The Brønsted acid catalytic system in 1,1,1,3,3,3‐hexafluoro‐2‐propanol was found to be particularly efficient for this transformation. This reaction can be extended to the synthesis of various phenol biaryls, including sterically hindered biaryls, with yields ranging from 58 to 90 % under mild reaction conditions and in a highly regiospecific manner.