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 | Zendy

Yu Tao | Zendy; Wu Xinyan | Zendy; Yang Jun | Zendy

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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.

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