Manganese-Catalyzed Direct Olefination of Methyl-Substituted Heteroarenes with Primary Alcohols

Angew Chem Int Ed Engl. 2018 Jul 16;57(29):9126-9130. doi: 10.1002/anie.201804729. Epub 2018 Jun 14.

Abstract

Herein, we present the first catalytic direct olefination of methyl-substituted heteroarenes with primary alcohols through an acceptorless dehydrogenative coupling. The reaction is catalyzed by a complex of the earth-abundant transition metal manganese that is stabilized by a bench-stable NNN pincer ligand derived from 2-hydrazinylpyridine. The reaction is environmentally benign, producing only hydrogen and water as byproducts. A large number of E-disubstituted olefins were selectively obtained with high efficiency.

Keywords: dehydrogenative coupling; heteroarenes; manganese; olefination; pincer ligands.