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Bifunctional Amine‐Squaramide Catalyzed Friedel–Crafts Alkylation Based on ortho ‐Quinone Methides in Oil‐Water Phases: Enantioselective Synthesis of Triarylmethanes
Author(s) -
Wang Yifeng,
Zhang Cheng,
Wang Haojiang,
Jiang Yidong,
Du Xiaohua,
Xu Danqian
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201600814
Subject(s) - chemistry , enantioselective synthesis , squaramide , bifunctional , friedel–crafts reaction , alkylation , catalysis , organic chemistry , bifunctional catalyst , amine gas treating , organocatalysis , yield (engineering) , materials science , metallurgy
An efficient enantioselective Friedel–Crafts alkylation reaction of electron‐rich β‐naphthol with in situ generated ortho ‐quinone methides catalyzed by chiral bifunctional amine‐squaramide catalysts has been developed. The chiral triarylmethane derivatives were obtained in good to high yields (up to 97% yield) with high enantioselectivities (up to 97% ee ) for most substrates under mild conditions. This study also revealed that the oil‐water biphase could significantly improve the efficiency of this catalytic system.