Sustainable Alkylation of Nitriles with Alcohols by Manganese Catalysis

Jannik C. Borghs, Mai Anh Tran, Jan Sklyaruk, Magnus Rueping, Osama El-Sepelgy

Research output: Contribution to journalArticlepeer-review

24 Scopus citations

Abstract

A general and chemoselective catalytic alkylation of nitriles using a homogeneous nonprecious manganese catalyst is presented. This alkylation reaction uses naturally abundant alcohols and readily available nitriles as coupling partners. The reaction tolerates a wide range of functional groups and heterocyclic moieties, efficiently providing useful cyanoalkylated products with water as the only side product. Importantly, methanol can be used as a C1 source and the chemoselective C-methylation of nitriles is achieved. The mechanistic investigations support the multiple role of the metal–ligand manganese catalyst, the dehydrogenative activation of the alcohol, α-C–H activation of the nitrile, and hydrogenation of the in-situ-formed unsaturated intermediate.
Original languageEnglish (US)
Pages (from-to)7927-7935
Number of pages9
JournalThe Journal of Organic Chemistry
Volume84
Issue number12
DOIs
StatePublished - May 22 2019

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