Organic Chemistry Frontiers 2018-04-04

α,β-Diaryl unsaturated ketones via palladium-catalyzed ring-opening of cyclopropenones with organoboronic acids

Lidong Shan, Ge Wu, Miaochang Liu, Wenxia Gao, Jinchang Ding, Xiaobo Huang, Huayue Wu

Index: 10.1039/C8QO00241J

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Abstract

Palladium-catalyzed ring-opening acylation of cyclopropenones with organoboronic acids at room temperature has been developed. Both arylboronic acids and vinylboronic acids are viable in this acylation reaction, providing a new protocol to synthesise α,β-diaryl unsaturated ketones with good yields and excellent stereospecificity. Preliminary mechanistic studies indicated that a vinylpalladium intermediate was generated in this procedure.