Organic Chemistry Portal

Abstracts

Search:

Copper-Catalyzed Aerobic Oxidative/Decarboxylative Phosphorylation of Aryl Acrylic Acids with P(III)-Nucleophiles

Biquan Xiong*, Lulu Si, Longzhi Zhu*, Yu Liu, Weifeng Xu, Ke-Wen Tang, Shuang-Feng Yin, Peng-Cheng Qian and Wai-Yeung Wong*

*Hunan Institute of Science and Technology, Yueyang; Hong Kong Polytechnic University, Hong Kong, P. R. China, Email: xiongbiquan126.com, zhulongzhihnu.edu.cn, wai-yeung.wongpolyu.edu.hk

B. Xiong, L. Si, L. Zhu, Y. Liu, W. Xu, K.-W. Tang, S.-F. Yin, P.-C. Qian, W.-Y. Wong, J. Org. Chem., 2023, 88, 12502-12518.

DOI: 10.1021/acs.joc.3c01238



see article for more reactions

Abstract

A copper-catalyzed aerobic oxidative/decarboxylative phosphorylation of aryl acrylic acids with P(III)-nucleophiles via the Michaelis-Arbuzov rearrangement provides β-ketophosphine oxides, β-ketophosphinates, and β-ketophosphonates in very good yields. The present reaction could be conducted effectively without the use of a ligand and a base.

see article for more examples

proposed mechanism



Key Words

phosphine oxides, phosphinates, phosphonates, Arbuzov reaction, oxygen


ID: J42-Y2023