Chemoselective semihydrogenation of alkynes catalyzed by manganese(I)-PNP pincer complexes

Marcel Garbe; Svenja Budweg; Veronica Papa; Zhihong Wei; Helen Hornke; Stephan Bachmann; Michelangelo Scalone; Anke Spannenberg; Haijun Jiao; Kathrin Junge; Matthias Beller

doi:10.1039/D0CY00992J

Chemoselective semihydrogenation of alkynes catalyzed by manganese(i)-PNP pincer complexes†‡

Marcel Garbe,§^a Svenja Budweg,

§^a Veronica Papa,

^a Zhihong Wei,

^a Helen Hornke,^a Stephan Bachmann,^b Michelangelo Scalone,^b Anke Spannenberg,^a Haijun Jiao,

^a Kathrin Junge

*^a and Matthias Beller

*^a

Author affiliations

* Corresponding authors

^a Leibniz-Institut für Katalyse e.V, Albert-Einstein-Straße 29a, Rostock, Germany
E-mail: Kathrin.Junge@catalysis.de, Matthias.Beller@catalysis.de

^b F. Hoffmann-La Roche AG, Department of Process Chemistry & Catalysis, Basel, Switzerland

Abstract

A general manganese catalyzed chemoselective semihydrogenation of alkynes to olefins in the presence of molecular hydrogen is described. The best results are obtained by applying the aliphatic Mn PNP pincer complex Mn-3c which allows the transformation of various substituted internal alkynes to the respective Z-olefins under mild conditions and in high yields. Mechanistic investigations based on experiments and computations indicate the formation of the Z-isomer via an outer-sphere mechanism.

Catalysis Science & Technology

Chemoselective semihydrogenation of alkynes catalyzed by manganese(i)-PNP pincer complexes†‡

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