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Blue Light-Emitting Diode-Induced Direct C-H Functionalization of 1,4-Quinones with Aryl and Alkyl Boronic Acids

Souvik Guha, Tejas Prabakar and Subhabrata Sen*

*Department of Chemistry, School of Natural Sciences, Shiv Nadar University, Dadri, Chithera, Greater Noida, UP 201314, India, Email: subhabrata.sensnu.edu.in

S. Guha, T. Prakabar, S. Sen, J. Org. Chem., 2022, 87, 15421-15434.

DOI: 10.1021/acs.joc.2c01972


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Abstract

The use of blue light-emitting diodes (LEDs) enables a direct functionalization of numerous 1,4-quinones with various aryl boronic acids at room temperature in an open flask without any catalysts and base in acetonitrile. With diverse 1,4-quinones like 1,4-benzo-, naphtho-, anthra-, and 4-bromonaphthoquinones, facile cross coupling reactions occur with aryl and alkyl boronic acids.

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proposed mechanism



Key Words

Cyclic Enones, Arylation, Photochemistry


ID: J42-Y2022