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,
zhulongzhi
hnu.edu.cn, wai-yeung.wong
polyu.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
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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.
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proposed mechanism
Key Words
phosphine oxides, phosphinates, phosphonates, Arbuzov reaction, oxygen
ID: J42-Y2023