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Tandem Acceptorless Dehydrogenative Coupling–Decyanation under Nickel Catalysis

Siba P. Midya, Murugan Subaramanian, Reshma Babu, Vinita Yadav, Ekambaram Balaraman

2021The Journal of Organic Chemistry24 citationsDOI

Abstract

The development of new catalytic processes based on abundantly available starting materials by cheap metals is always a fascinating task and marks an important transition in the chemical industry. Herein, a nickel-catalyzed acceptorless dehydrogenative coupling of alcohols with nitriles followed by decyanation of nitriles to access diversely substituted olefins is reported. This unprecedented C═C bond-forming methodology takes place in a tandem manner with the formation of formamide as a sole byproduct. The significant advantages of this strategy are the low-cost nickel catalyst, good functional group compatibility (ether, thioether, halo, cyano, ester, amino, N/O/S heterocycles; 43 examples), synthetic convenience, and high reaction selectivity and efficiency.

Topics & Concepts

TandemCatalysisChemistryThioetherNickelCombinatorial chemistryHalideEtherOrganic chemistryMaterials scienceComposite materialAsymmetric Hydrogenation and CatalysisCatalytic C–H Functionalization MethodsCarbon dioxide utilization in catalysis
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