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Coupling of Quinone Monoacetals Promoted by Sandwiched Brønsted Acids: Synthesis of Oxygenated Biaryls
Author(s) -
Dohi Toshifumi,
Washimi Naohiko,
Kamitanaka Tohru,
Fukushima Keiichiro,
Kita Yasuyuki
Publication year - 2011
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.201101646
Subject(s) - quinone , chemistry , brønsted–lowry acid–base theory , nucleophile , combinatorial chemistry , coupling (piping) , catalysis , organic chemistry , materials science , metallurgy
Unusual protons: Brønsted acids sandwiched between sheets of solid acids, such as montmorillonites, activated quinone monoacetals 1 to selectively react with aromatic nucleophiles 2 in an unprecedented substitution reaction. The synthetic utility of the strategy for obtaining highly oxygenated biaryls 3 is highlighted by the synthesis of gilvocarcin aglycones.