Lewis Acid Promoted Aerobic Oxidative Coupling of Thiols with Phosphonates by Simple Nickel(II) Catalyst: Substrate Scope and Mechanistic Studies

Jing-Wen Xue, Miao Zeng, Sicheng Zhang, Zhuqi Chen, Guochuan Yin*

*School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan 430074, P.R. China, Email: gyinhust.edu.cn

J.-W. Xue, M. Zeng, S. Zhang, Z. Chen, G. Yin, J. Org. Chem., 2019, 84, 4179-4190.

DOI: 10.1021/acs.joc.9b00194

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Abstract

With Ni(OAc)₂ as catalyst, an oxidative coupling of thiols and phosphonates to phosphorothioates with oxygen as oxidant proceeded very sluggishly with low yield, whereas adding non-redox-active metal ions such as Y³⁺ dramatically promoted the catalytic efficiency. Y(OTf)₃ can obviously accelerate the activation of thiols by Ni(II) and next accelerate its reaction with phosphonate.

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Key Words

phosphorothioates, oxygen

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ID: J42-Y2019