A Visible Light Driven Nickel Carbonylation Catalyst: The Synthesis of Acid Chlorides from Alkyl Halides.

Autor: El Chami K; Department of Chemistry, McGill University, 801 Sherbrooke Street West, H3A0B8, Montreal, QC, Canada., Liu Y; Department of Chemistry, McGill University, 801 Sherbrooke Street West, H3A0B8, Montreal, QC, Canada., Belahouane MA; Department of Chemistry, McGill University, 801 Sherbrooke Street West, H3A0B8, Montreal, QC, Canada., Ma Y; Department of Chemistry, McGill University, 801 Sherbrooke Street West, H3A0B8, Montreal, QC, Canada., Lagueux-Tremblay PL; Department of Chemistry, McGill University, 801 Sherbrooke Street West, H3A0B8, Montreal, QC, Canada., Arndtsen BA; Department of Chemistry, McGill University, 801 Sherbrooke Street West, H3A0B8, Montreal, QC, Canada.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2023 Mar 01; Vol. 62 (10), pp. e202213297. Date of Electronic Publication: 2023 Jan 25.
DOI: 10.1002/anie.202213297
Abstrakt: We describe here the development of a visible light driven nickel carbonylation catalyst. The combination of the large bite-angle Xantphos ligand with nickel(0) generates a catalyst capable of activating alkyl halides toward carbonylation at ambient temperature in the presence of blue light irradiation, and the reductive elimination of high energy acid chloride products. Unlike classical carbonylations, where the coordination of carbon monoxide inhibits the reactivity of earth abundant nickel catalysts, a CO-associated nickel is found to be the active catalyst in the reaction. Coupling the build-up of acid chlorides with nucleophile addition can be used to access various amides, esters and thioesters, including those of sterically encumbered substrates or with metal-reactive functionalities.
(© 2022 Wiley-VCH GmbH.)
Databáze: MEDLINE
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