Synlett 2023; 34(14): 1715-1718
DOI: 10.1055/s-0042-1751448
letter

Solvent-Free Tandem Reaction of P(O)–OH and an Epichlorohydrocarbon for Controllable O-Alkylation through a Ring-Opening and Annulation Process

Jia Yang
a   Central South University, College of Chemistry and Chemical Engineering, and Hunan Provincial Key Laboratory of Efficient and Clean Utilization of Manganese Resources, No. 932 South Lushan Road, Changsha Hunan 410083, P. R. of China
,
Yi Luo
a   Central South University, College of Chemistry and Chemical Engineering, and Hunan Provincial Key Laboratory of Efficient and Clean Utilization of Manganese Resources, No. 932 South Lushan Road, Changsha Hunan 410083, P. R. of China
,
Yirui Huang
b   Changsha Medical University, Hunan Key Laboratory for the Research and Development of Novel Pharmaceutical Preparations, No. 1 Leifeng Road, Changsha, 410219, P. R. of China
,
Zixuan Wang
b   Changsha Medical University, Hunan Key Laboratory for the Research and Development of Novel Pharmaceutical Preparations, No. 1 Leifeng Road, Changsha, 410219, P. R. of China
,
Wenyu Chen
b   Changsha Medical University, Hunan Key Laboratory for the Research and Development of Novel Pharmaceutical Preparations, No. 1 Leifeng Road, Changsha, 410219, P. R. of China
,
Liang Zhu
b   Changsha Medical University, Hunan Key Laboratory for the Research and Development of Novel Pharmaceutical Preparations, No. 1 Leifeng Road, Changsha, 410219, P. R. of China
,
Huihui Yuan
a   Central South University, College of Chemistry and Chemical Engineering, and Hunan Provincial Key Laboratory of Efficient and Clean Utilization of Manganese Resources, No. 932 South Lushan Road, Changsha Hunan 410083, P. R. of China
,
Qian Xu
b   Changsha Medical University, Hunan Key Laboratory for the Research and Development of Novel Pharmaceutical Preparations, No. 1 Leifeng Road, Changsha, 410219, P. R. of China
,
Shuai Wang
a   Central South University, College of Chemistry and Chemical Engineering, and Hunan Provincial Key Laboratory of Efficient and Clean Utilization of Manganese Resources, No. 932 South Lushan Road, Changsha Hunan 410083, P. R. of China
,
Hong Zhong
a   Central South University, College of Chemistry and Chemical Engineering, and Hunan Provincial Key Laboratory of Efficient and Clean Utilization of Manganese Resources, No. 932 South Lushan Road, Changsha Hunan 410083, P. R. of China
› Author Affiliations
Financial support from the National Natural Science Foundation of China (No. 21902185), the Natural Science Foundation of Hunan Province (No. 2019JJ50748), and the Fundamental Research Funds for the Central Universities of Central South University is gratefully acknowledged.


Abstract

We report an efficient additive- and solvent-free O-alkylation of P(O)–OH compounds with epichlorohydrocarbons for the synthesis of epoxy-group-containing phosphinates. The transformation proceeds through a tandem reaction involving ring-opening and annulation processes. The ring-opened products and dechlorinated products can be obtained selectively by controlling the reaction conditions. This protocol is expected to be useful in industry because it is readily scaled up to a gram level and involves simple posttreatment.

Supporting Information



Publication History

Received: 05 February 2023

Accepted after revision: 11 April 2023

Article published online:
26 April 2023

© 2023. Thieme. All rights reserved

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