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Divergent Palladium‐Catalyzed Tandem Reaction of Cyanomethyl Benzoates with Arylboronic Acids: Synthesis of Oxazoles and Isocoumarins
Author(s) -
Dai Ling,
Yu Shuling,
Xiong Wenzhang,
Chen Zhongyan,
Xu Tong,
Shao Yinlin,
Chen Jiuxi
Publication year - 2020
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.202000125
Subject(s) - benzoates , isocoumarins , chemistry , catalysis , palladium , organic chemistry , aryl , medicinal chemistry , combinatorial chemistry , alkyl
A palladium‐catalyzed tandem reaction of cyanomethyl benzoates with arylboronic acids has been achieved. Substitution at the 2‐position of cyanomethyl benzoates was found to be crucial for the selective synthesis of oxazoles and isocoumarins. Cyanomethyl benzoates afforded 2,4‐diaryloxazoles as products, while 2‐benzoyl‐substituted cyanomethyl benzoates delivered 3‐benzoyl‐4‐aryl‐isocoumarins selectively. Furthermore, a possible mechanism for the selective reaction of cyanomethyl benzoates with arylboronic acids was discussed.