An Efficient Synthesis of 1-Arylvinylphosphonates via Direct Functionalization of C (sp3)—H Bond

doi:10.6023/cjoc201803016

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (10): 2791-2797.DOI: 10.6023/cjoc201803016 Previous Articles Next Articles

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通过C(sp³)—H键直接官能团化高效合成1-芳基烯基膦酸酯

任林静, 冉茂刚, 方学红, 赵玲, 姚秋丽

遵义医学院药学院遵义 56300

收稿日期:2018-03-13 修回日期:2018-05-05 发布日期:2018-06-01
通讯作者: 姚秋丽,E-mail:yao.qiuli@zmc.edu.cn E-mail:yao.qiuli@zmc.edu.cn
基金资助:
国家自然科学基金（Nos.21462056，21801261）、贵州省联合基金（No.[2014]7542）和遵义医学院（Nos.20163715，F-627）资助项目.

An Efficient Synthesis of 1-Arylvinylphosphonates via Direct Functionalization of C (sp³)—H Bond

Ren Linjing, Ran Maogang, Fang Xuehong, Zhao Ling, Yao Qiuli

School of Pharmacy, Zunyi Medical University, Zunyi 56300

Received:2018-03-13 Revised:2018-05-05 Published:2018-06-01
Contact: 10.6023/cjoc201803016 E-mail:yao.qiuli@zmc.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21462056, 21801261), the Science and Technology Foundation of Guizhou Province (No.[2014]7542) and the Zunyi Medical University (Nos. 20163715, F-627).

1. An Efficient Synthesis of 1-Arylvinylphosphonates via Direct Functionalization of C (sp³)—H Bond.PDF(1457KB)

Abstract

The direct functionalization of the C (sp³)—H bond adjacent to the phosphonate group for the preparation of vinyl phosphonates was rarely developed. Herein, a simple and efficient tetrabutylammonium iodide catalyzed protocol for the preparation of vinyl phosphonates from benzylic phosphonates and paraformaldehyde is achieved under mild conditions in air. Moderate to high yields can be obtained for a broad scope of substrates.

Key words: phosphonate, olefination, C(sp³)—H functionalization, Horner-Wadsworth-Emmons reaction

Cite this article

Ren Linjing, Ran Maogang, Fang Xuehong, Zhao Ling, Yao Qiuli. An Efficient Synthesis of 1-Arylvinylphosphonates via Direct Functionalization of C (sp³)—H Bond[J]. Chin. J. Org. Chem., 2018, 38(10): 2791-2797.

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通过C(sp³)—H键直接官能团化高效合成1-芳基烯基膦酸酯

An Efficient Synthesis of 1-Arylvinylphosphonates via Direct Functionalization of C (sp³)—H Bond

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通过C(sp3)—H键直接官能团化高效合成1-芳基烯基膦酸酯