Work

Cobalt-Catalyzed Syntheses of Acrylamides and Succindiamides from Alkynes and Amines Promoted by Light

Year: 2026

Type: article

Abstract: Catalytic hydrocarbonylations of alkynes hold potential for highly atom-economical and sustainable syntheses of α,β-unsaturated carboxylic acid derivatives. Alkyne hydroaminocarbonylations deliver valuable acrylamides in couplings with amine nucleophiles, but current approaches are limited in scope and rely on precious metal catalysts. Herein, we report a catalytic hydroaminocarbonylation of alkynes using cobalt carbonyl catalysts promoted by visible light. In contrast to the diverse alkene hydrocarbonylations catalyzed by cobalt carbonyl, applications in alkyne hydrocarbonylation are virtually unknown. The reaction couples a broad range of amines with terminal and internal alkynes, and simple reaction modification enables the syntheses of succindiamides in a stereoselective fashion. Alkyne hydroaminocarbonylation is viable even in the absence of a reaction solvent, highlighting the sustainability of this process. Computational and experimental investigations of both the single and double hydroaminocarbonylations support a key role of the cobalt tricarbonyl anion in substrate activation, leading to high reaction regio- and stereoselectivities.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.6c01395

Authors: Jack T. Hemphill, Dylan T. Hsu, Alexandra D. Handlin, Shubin Liu, Erik J. Alexanian

Institution: University of North Carolina at Chapel Hill

Language: English

Topic: Catalytic Alkyne Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Award: G3782323928