Divergent Palladium‐Catalyzed Tandem Reaction of Cyanomethyl Benzoates with Arylboronic Acids: Synthesis of Oxazoles and Isocoumarins
Ling Dai, Shuling Yu, Wenzhang Xiong, Zhongyan Chen, Tong Xu, Yinlin Shao, Jiuxi Chen
Abstract
Abstract 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. magnified image
Topics & Concepts
BenzoatesIsocoumarinsChemistryPalladiumCatalysisOrganic chemistryMedicinal chemistryCombinatorial chemistryCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsSynthesis and Biological Activity