Divergent Palladium‐Catalyzed Tandem Reaction of Cyanomethyl Benzoates with Arylboronic Acids: Synthesis of Oxazoles and Isocoumarins

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 prod...

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Veröffentlicht in:Advanced synthesis & catalysis 2020-04, Vol.362 (9), p.1893-1898
Hauptverfasser: Dai, Ling, Yu, Shuling, Xiong, Wenzhang, Chen, Zhongyan, Xu, Tong, Shao, Yinlin, Chen, Jiuxi
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Sprache:eng
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Zusammenfassung: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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202000125