K2CO3-promoted aerobic oxidative cross-coupling of trialkyl phosphites with thiophenols

Chunxiao Wen; Qian Chen; Yulin Huang; Xiaofeng Wang; Xinxing Yan; Jiekun Zeng; Yanping Huo; Kun Zhang

doi:10.1039/C7RA09057A

K₂CO₃-promoted aerobic oxidative cross-coupling of trialkyl phosphites with thiophenols†

Chunxiao Wen,^a Qian Chen,

*^ab Yulin Huang,^a Xiaofeng Wang,^a Xinxing Yan,^a Jiekun Zeng,^a Yanping Huo

^a and Kun Zhang*^a

Author affiliations

* Corresponding authors

^a School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006, China
E-mail: qianchen@gdut.edu.cn, kzhang@gdut.edu.cn
Fax: +86 20 3932 2235
Tel: +86 20 3932 2231

^b Key Laboratory of Functional Molecular Engineering of Guangdong Province, South China University of Technology, Guangzhou 510640, China

Abstract

Convenient, practical and economical phosphorylation of thiols has been achieved via halogen- and metal-free K₂CO₃-promoted aerobic oxidative cross-coupling of trialkyl phosphites, dimethyl phenylphosphonite, or methyl diphenylphosphinite with thiophenols using air as the oxidant at room temperature. This transformation provides a straightforward route to the construction of phosphorus–sulfur bonds with wide functional group compatibility, which affords phosphorothioates in up to 94% yield.

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DOI: https://doi.org/10.1039/C7RA09057A
Article type: Paper
Submitted: 16 aug 2017
Accepted: 18 sep 2017
First published: 25 sep 2017
This article is Open Access

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RSC Adv., 2017,7, 45416-45419

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K₂CO₃-promoted aerobic oxidative cross-coupling of trialkyl phosphites with thiophenols

C. Wen, Q. Chen, Y. Huang, X. Wang, X. Yan, J. Zeng, Y. Huo and K. Zhang, RSC Adv., 2017, 7, 45416 DOI: 10.1039/C7RA09057A

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