Rhodium-Catalyzed Deoxygenation and Borylation of Ketones: A Combined Experimental and Theoretical Investigation

Lei Tao, Xueying Guo, Jie Li, Ruoling Li, Zhenyang Lin* and Wanxiang Zhao*

*The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR; Hunan University, Changsha, Hunan 410082, China, Email: chzlinust.hk, zhaowanxianghnu.edu.cn

L. Tao, X. Guo, J. Li, R. Li, Z. Lin, W. Zhao, J. Am. Chem. Soc., 2020, 142, 18118-18127.

DOI: 10.1021/jacs.0c07854

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Abstract

Rhodium-catalyzed deoxygenations and borylations of ketones with B₂pin₂ provide alkenes, vinylboronates, and vinyldiboronates. These reactions offer mild reaction conditions, a broad substrate scope, and excellent functional-group compatibility. Mechanistic studies support that the ketones initially undergo a Rh-catalyzed deoxygenation to give alkenes via boron enolate intermediates.

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Key Words

reductive alkene formations, vinylboronates, bis(pinacolato)diboron

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ID: J48-Y2020