Highly Chemo- and Stereoselective Transfer Semihydrogenation of Alkynes Catalyzed by a Stable, Well-defined Manganese(II) Complex

Aleksandra Brzozowska, Luis Azofra Mesa, Viktoriia Zubar, Iuliana Atodiresei, Luigi Cavallo, Magnus Rueping, Osama El-Sepelgy

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88 Scopus citations

Abstract

The first example of manganese catalyzed semihydrogenation of internal alkynes to (Z)-alkenes using ammonia borane as a hydrogen donor is reported. The reaction is catalyzed by a pincer complex of the earth abundant manganese(II) salt in the absence of any additives, base or super hydride. The ammonia borane smoothly reduces the manganese pre-catalyst [Mn(II)-PNP][Cl]2 to the catalytically active species [Mn(I)-PNP]-hydride in the triplet spin state. This manganese hydride is highly stabilized by complexation with the alkyne substrate. Computational DFT analysis studies of the reaction mechanism rationalizes the origin of stereoselectivity towards formation of (Z)-alkenes.
Original languageEnglish (US)
Pages (from-to)4103-4109
Number of pages7
JournalACS Catalysis
Volume8
Issue number5
DOIs
StatePublished - Mar 30 2018

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: L.M.A. and L.C., acknowledge King Abdullah University of Science and Technology (KAUST) for support. Gratitude is also due to the KAUST Supercomputing Laboratory using the supercomputer Shaheen II for providing the computational resources.

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