Mn(OAc)3-mediated phosphonation–lactonization of alkenoic acids: synthesis of phosphono-γ-butyrolactones

Yuzhen Gao; Xueqin Li; Jian Xu; Yile Wu; Weizhu Chen; Guo Tang; Yufen Zhao

doi:10.1039/C4CC07978G

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Mn(OAc)₃-mediated phosphonation–lactonization of alkenoic acids: synthesis of phosphono-γ-butyrolactones†‡

Yuzhen Gao,^a Xueqin Li,^a Jian Xu,^a Yile Wu,^a Weizhu Chen,^ab Guo Tang*^a and Yufen Zhao^ac

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* Corresponding authors

^a Department of Chemistry, College of Chemistry and Chemical Engineering, and the Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen, Fujian 361005, China
E-mail: t12g21@xmu.edu.cn
Fax: +86-592-2185780

^b Third Institute Of Oceanography, State Oceanic Administration, Xiamen, Fujian 361005, China

^c Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, China

Abstract

A new, general method for the synthesis of phosphono-γ-butyrolactones has been achieved through Mn(OAc)₃-mediated radical oxidative phosphonation and lactonization of alkenoic acids with H-phosphonates and H-phosphine oxide. Mn(OAc)₃ can be readily prepared from Mn(OAc)₂ in the laboratory. This transformation allows the direct formation of a P–C bond and the construction of a lactone ring in one reaction.

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Article information

DOI: https://doi.org/10.1039/C4CC07978G
Article type: Communication
Submitted: 09 Oct 2014
Accepted: 07 Dec 2014
First published: 08 Dec 2014

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Chem. Commun., 2015,51, 1605-1607

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Mn(OAc)₃-mediated phosphonation–lactonization of alkenoic acids: synthesis of phosphono-γ-butyrolactones

Y. Gao, X. Li, J. Xu, Y. Wu, W. Chen, G. Tang and Y. Zhao, Chem. Commun., 2015, 51, 1605 DOI: 10.1039/C4CC07978G

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