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Radical Alkylcyanation of 1,6-Enynes with Isonitriles as Bifunctional Reagents

Zhonghou Huang, Jian Qin, Yuntong Hu, Shengqing Zhu, Lingling Chu

2024Organic Letters13 citationsDOI

Abstract

We report a radical cyano-cyclization of 1,6-enynes with isonitriles via photochemically driven nickel catalysis, forging alkenyl nitrile-tethered γ-lactams under mild conditions. This reaction leverages the photoexcitation of in situ generated nickel (isonitrile) species to facilitate isonitriles serving as alkyl radical precursors and cyanide sources. The reaction accommodates a wide range of substrates, exhibiting excellent regioselectivity and Z / E stereoselectivity.

Topics & Concepts

ChemistryBifunctionalReagentCombinatorial chemistryOrganic chemistryMedicinal chemistryCatalysisRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods
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