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Reduction of Aryl Halides into Arenes with 2-Propanol Promoted by a Substoichiometric Amount of a tert-Butoxy Radical Source

Ryota Ueno, Takashi Shimizu, Eiji Shirakawa*

*Department of Applied Chemistry for Environment, School of Science and Technology, Kwansei Gakuin University, Sanda, Hyogo 669-1337, Japan, Email: eshirakawakwansei.ac.jp

R. Ueno, T. Shimizu, E. Shirakawa, Synlett, 2016, 27, 747-744.

DOI: 10.1055/s-0035-1561342 (free Supporting Information)


Abstract

Aryl halides are reduced into the corresponding arenes in high yields, using 2-propanol as reductant and solvent, cesium carbonate as base, and di-tert-butyl peroxide (or di-tert-butyl hyponitrite) as radical initiator. This simple system reduces various aryl bromides and iodides through a SET mechanism with high functional-group tolerance.

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Key Words

reduction, radical chain mechanism, anion radical, ketyl, tert-butoxy radical, isopropanol


ID: J60-Y2016