Effective Transformation of Alkynylphosphonates into β-Ketophosphonates with a Gold(I) Catalyst

doi:10.6023/cjoc201404046

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (10): 2007-2014.DOI: 10.6023/cjoc201404046 Previous Articles Next Articles

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金催化炔基膦酸酯水合反应合成β-羰基膦酸酯

刘开建, 刘宏伟, 王文革, 欧丽娟, 王津津, 胡波年

湖南工学院材料与化学工程系衡阳 421002

收稿日期:2014-04-24 修回日期:2014-09-03 发布日期:2014-09-09
通讯作者: 刘开建, 胡波年 E-mail:liukaijian_1982@163.com;hbonian@163.com
基金资助:
湖南省科技计划（No. 2014FJ3053）、国家自然科学基金（No. 21176061）、湖南省自然科学基金（No. 13JJ3132）、湖南省重点建设学科和衡阳市科技计划资助项目.

Effective Transformation of Alkynylphosphonates into β-Ketophosphonates with a Gold(I) Catalyst

Liu Kaijian, Liu Hongwei, Wang Wenge, Ou Lijuan, Wang Jingjing, Hu Bonian

Department of Materials and Chemical Engineering, Hunan Institute of Technology, Hengyang 421002

Received:2014-04-24 Revised:2014-09-03 Published:2014-09-09
Supported by:
Project supported by the Science and Technology Planning Project of Hunan Province (No. 2014FJ3053), the National Natural Science Foundation of China (No. 21176061), the Natural Science Foundation of Hunan Province (No. 13JJ3132), the Construct Program of the Key Discipline in Hunan Province and Science and Technology Planning Project of Hengyang City (No. 2014FJ3053).

1. Effective Transformation of Alkynylphosphonates into β-Ketophosphonates with a Gold(I) Catalyst.PDF(782KB)

Abstract

β-Ketophosphonates are an important class of carbonyl compounds which exhibit a wide range of biological activities and outstanding metal-complexing abilities. They are building blocks in organic synthesis, especially as intermediates for the synthesis of α,β-unsaturated carbonyl compounds, chrial β-hydroxy and β-hydroxy phosphonic acids. In this paper, a simple, convenient and environmentally benign method to synthesize the β-ketophosphonates from alkynylphosphonates was developed, which can be easily prepared in one step from commercial terminal alkynes. In the presence of 2.5 mol% XPhosAuSbF₆ and 3 equiv. of water in dichloroethane at room temperature, a broad range of alkynylphosphonates were converted into the corresponding β-ketophosphonates in nearly equivalent conversion through gold-catalyzed hydration reaction. The presented methodology will provide new strategies for β-ketophosphonates-type natural product and drug synthesis, which has important academic significance and application value.

Key words: alkynylphosphonates, β-ketophosphonate, gold catalysis, hydration reaction

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Liu Kaijian, Liu Hongwei, Wang Wenge, Ou Lijuan, Wang Jingjing, Hu Bonian. Effective Transformation of Alkynylphosphonates into β-Ketophosphonates with a Gold(I) Catalyst[J]. Chin. J. Org. Chem., 2014, 34(10): 2007-2014.

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金催化炔基膦酸酯水合反应合成β-羰基膦酸酯

Effective Transformation of Alkynylphosphonates into β-Ketophosphonates with a Gold(I) Catalyst

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