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

doi:10.6023/cjoc201805027

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (8): 1977-1984.DOI: 10.6023/cjoc201805027 Previous Articles Next Articles

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盐酸促进、铜/铁共催化2-取代丙烯酸酯与膦氧类化合物的脱酯氧膦化反应

王华斌^a,b, 付强^c, 张智杰^c,d, 高明^a,b, 姬建新^a, 易东^c

a 中国科学院成都生物研究所成都 610041;
b 中国科学院大学北京 100049;
c 西南医科大学药学院泸州 646000;
d 西南医科大学药物研究中心泸州 646000

收稿日期:2018-05-11 修回日期:2018-05-30 发布日期:2018-06-01
通讯作者: 易东 E-mail:yidong@swmu.edu.cn
基金资助:
国家自然科学基金（No.21572217）、中国科学院战略生物资源服务网络计划（No.ZSTH-001）和西南医科大学校级科研基金（No.2017-ZRZD-020）资助项目.

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

Received:2018-05-11 Revised:2018-05-30 Published:2018-06-01
Contact: 10.6023/cjoc201805027 E-mail:yidong@swmu.edu.cn
Supported by:
Project 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).

1. Hydrochloric Acid-Promoted Copper/Iron-Cocatalyzed Deesterifica-tive Oxyphosphorylation of 2-Substituted Acrylates with H-Phosphine Oxides.PDF(2112KB)

Abstract

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.

Key words: β-ketophosphine oxides, 2-substituted acrylates, hydrochloric acid, copper/iron-cocatalysis, dioxygen

Cite this article

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]. Chin. J. Org. Chem., 2018, 38(8): 1977-1984.

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盐酸促进、铜/铁共催化2-取代丙烯酸酯与膦氧类化合物的脱酯氧膦化反应

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

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