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Cascade Synthesis of 4‐Arylcoumarins: Pd‐Catalyzed Arylations and Cyclizations with ( E )‐Ethyl 3‐(2‐Hydroxyaryl)acrylates and Triarylantimony Difluorides
Author(s) -
Kitamura Yuki,
Matsumura Mio,
Kato Yukari,
Murata Yuki,
Yasuike Shuji
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901866
Subject(s) - difluoride , chemistry , catalysis , organic chemistry , aryl , oxidative coupling of methane , medicinal chemistry , combinatorial chemistry , polymer chemistry , alkyl
Herein, we describe a simple general method for the synthesis of 4‐arylcoumarins using pentavalent organoantimony compounds. The reactions of 3‐(2‐hydroxyaryl)acrylates with triarylantimony difluorides in the presence of Pd(OAc) 2 (10 mol‐%) and 2,2'‐bipyridyl (10 mol‐%) at 80 °C under aerobic conditions afforded 4‐arylcoumarins in good‐to‐excellent yields. This protocol involves a cascade oxidative Heck‐type arylation followed by cyclization, with all the aryl groups in the triarylantimony difluoride transferred to the coupling products. Triarylantimony difluorides resulted in better outcomes than those obtained with other pentavalent organoantimony or bismuth compounds.