1. Efficient Coupling Reaction of Quinone Monoacetal with Phenols Leading to Phenol Biaryls
- Author
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Daichi Koseki, Yasuyuki Kita, Tohru Kamitanaka, Kohei Tsuboshima, Koji Morimoto, Hitoho Takamuro, and Toshifumi Dohi
- Subjects
Steric effects ,Reaction mechanism ,010405 organic chemistry ,Chemistry ,General Medicine ,General Chemistry ,010402 general chemistry ,01 natural sciences ,Catalysis ,Coupling reaction ,0104 chemical sciences ,Quinone ,chemistry.chemical_compound ,Organic chemistry ,Phenol ,Phenols ,Brønsted–Lowry acid–base theory - Abstract
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.
- Published
- 2016
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