Journal
ACS OMEGA
Volume 4, Issue 6, Pages 10279-10292Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acsomega.9b01387
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Funding
- COST Action [CA15106]
- Special Account for Research Grants of the National and Kapodistrian University of Athens [70/3/14872]
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Tetrasubstituted propargylamines comprise a unique class of highly useful compounds, which can be accessed through the multicomponent coupling between ketones, amines, and alkynes (KA(2) coupling), an underexplored transformation. Herein, the development of a novel, highly efficient, and user-friendly catalytic system for the KA(2) coupling, based on the environmentally benign, inexpensive, and readily available zinc acetate, is described. This system is employed in the multicomponent assembly of unprecedented, tetrasubstituted propargylamines derived from structurally diverse, challenging, and even biorelevant substrates. Notable features of this protocol include the demonstration of the enhancing effect that neat conditions can have on catalytic activity, as well as the expedient functionalization of hindered, prochiral cyclohexanones, linear ketones, and interesting molecular scaffolds such as norcamphor and nornicotine.
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