Citation: Wang Huabin, Fu Qiang, Zhang Zhijie, Gao Ming, Ji Jianxin, Yi Dong. Hydrochloric Acid-Promoted Copper/Iron-Cocatalyzed Deesterifica-tive Oxyphosphorylation of 2-Substituted Acrylates with H-Phosphine Oxides[J]. Chinese Journal of Organic Chemistry, ;2018, 38(8): 1977-1984. doi: 10.6023/cjoc201805027 shu

Hydrochloric Acid-Promoted Copper/Iron-Cocatalyzed Deesterifica-tive Oxyphosphorylation of 2-Substituted Acrylates with H-Phosphine Oxides

Wang Huabin ^a,b ,
Fu Qiang ^c ,
Zhang Zhijie ^c,d ,
Gao Ming ^a,b ,
Ji Jianxin ^a ,
Yi Dong ^c,,

a.
Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041
b.
University of the Chinese Academy of Sciences, Beijing 100049
c.
School of Pharmacy, Southwest Medical University, Luzhou 646000
d.
Drug Discovery Reseach Center, Southwest Medical University, Luzhou 646000

Corresponding author: Yi Dong, yidong@swmu.edu.cn
Received Date: 11 May 2018
Revised Date: 30 May 2018
Available Online: 31 August 2018
Fund Project: the Strategic Biological Resources Service Network Program of Chinese Academy of Sciences ZSTH-001the National Natural Science Foundation of China 21572217Project supported by the National Natural Science Foundation of China (No. 21572217), the Strategic Biological Resources Service Network Program of Chinese Academy of Sciences (No. ZSTH-001) and the Scientific Research Foundation of Southwest Medical University (No. 2017-ZRZD-020)the Scientific Research Foundation of Southwest Medical University 2017-ZRZD-020

Figures(3)

An unprecedented method for the transformation of 2-substituted acrylates into β-ketophosphine oxides has successfully been developed via hydrochloric acid-promoted copper/iron-cocatalyzed deesterificative oxyphosphorylation under dioxygen atmosphere, simultaneously inhibiting the formation of the preceding hydroxyphosphorylation products. Through this convenient and practical process, a library of structurally diverse β-ketophosphine oxides could be selectively and effectively obtained with broad substrate scope and good functional group tolerance under mild conditions, accompanied by chemoselective cleavage of C(sp²)-C(C=O) bonds.
- β-ketophosphine oxides,
- 2-substituted acrylates,
- hydrochloric acid,
- copper/iron-cocatalysis,
- dioxygen
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