Electrochemically Enabled Carbohydroxylation of Alkenes with HO and Organotrifluoroborates.

J Am Chem Soc

State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, Innovative Collaboration Center of Chemistry for Energy Materials, and College of Chemistry and Chemical Engineering , Xiamen University, Xiamen 361005 , P. R. China.

Published: December 2018

Unprecedented hydroxy-alkynylation and -alkenylation reactions of arylalkenes have been developed through electrochemically enabled addition of an organotrifluoroborate reagent and HO across the double bond of the alkene. The use of electrochemistry to promote these oxidative alkene 1,2-difunctionalization reactions not only obviates the need for transition-metal catalysts and oxidizing reagents but also ensures high regio- and chemoselectivity to afford homopropargylic or homoallylic alcohols. The possibility of extending the electrochemical alkene difunctionalization strategy to other alkene carbo-heterofunctionalization reactions has been demonstrated.

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http://dx.doi.org/10.1021/jacs.8b08592DOI Listing

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