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A New Synthetic Method of ( Z )‐4‐Aryl‐but‐2‐en‐1‐ols via Suzuki‐Miyaura Cross‐Coupling Reaction of 4‐Substituted 1,2‐Oxaborol‐2(5 H )‐ols with Benzyl Bromides
Author(s) -
Yu Tao,
Wu Xinyan,
Yang Jun
Publication year - 2012
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201201122
Subject(s) - chemistry , aryl , yield (engineering) , selectivity , coupling reaction , choleretic , suzuki reaction , medicinal chemistry , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , medicine , alkyl , materials science , metallurgy , endocrinology
Z and E configuration 4‐aryl‐but‐2‐en‐1‐ols were isolated from several terrestrial plants, and ( Z )‐4‐aryl‐but‐2en‐1‐ols were found to have choleretic activity. Strategies have been reported to synthesize ( E )‐4‐aryl‐but‐2‐en‐1ols with high selectivity. However, there is no method to obtain ( Z )‐4‐aryl‐but‐2‐en‐1‐ols with high selectivity now. We developed a Suzuki‐Miyaura cross‐coupling reaction of 1,2‐oxaborol‐2(5 H )‐ols with benzyl bromides to synthesize ( Z )‐4‐aryl‐but‐2‐en‐1‐ols, the products were obtained in up to 94% isolated yield.