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Electrochemistry-Enabled Ir-Catalyzed Vinylic C−H Functionalization

preprint
submitted on 10.09.2019 and posted on 11.09.2019 by Qi-Liang Yang, Yi-Kang Xing, Xiang-Yang Wang, Hong-Xing Ma, Xin-Jun Weng, Xiang Yang, Hai-Ming Guo, tian-sheng mei
Synergistic use of electrochemistry and organometallic catalysis has emerged as a powerful tool for site-selective C–H functionalization, yet this type of transformation has thus far mainly been limited to arene C–H functionalization. Herein, we report the development of electrochemical vinylic C–H functionalization of acrylic acids with alkynes. In this reaction an iridium catalyst enables C–H/O–H functionalization for alkyne annulation, affording a-pyrones with good to excellent yields in an undivided cell. Preliminary mechanistic studies show that anodic oxidation is crucial for releasing the product and regeneration of a Ir(III) intermediate from a diene-Ir(I)complex, which is a coordinatively saturated, 18-electron complex. Importantly, common chemical oxidants such as Ag(I) or Cu(II) did not give significant amounts of the desired product in the absence of electrical current under otherwise identical conditions.

History

Email Address of Submitting Author

mei7900@sioc.ac.cn

Institution

Shanghai Institute of Organic Chemistry

Country

China

ORCID For Submitting Author

0000-0002-4985-1071

Declaration of Conflict of Interest

no confict interest

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in Journal of the American Chemical Society

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