Coupling of Quinone Monoacetals Promoted by Sandwiched Brønsted Acids: Synthesis of Oxygenated Biaryls | Zendy

Dohi Toshifumi | Zendy; Washimi Naohiko | Zendy; Kamitanaka Tohru | Zendy; Fukushima Keiichiro | Zendy; Kita Yasuyuki | Zendy

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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.

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