Three-Component Syntheses of Functionalized Selenocyanates

Abstract

A metal-free Meerwein-type arylation protocol of α,β-unsaturated compounds is reported. 4-Aryl-3-selenocyanatobutan-2-ones, methyl 3-aryl-2-selenocyanatopropanoates, 3-aryl-2-selenocyanatopropanenitriles, and 1-aryl-2-phenyl-2-selenocyanatoethanes were prepared by a selenocyanatoarylation reaction from easily available arenediazonium tetrafluoroborates, potassium selenocyanate, and methyl vinyl ketone, methyl acrylate, acrylonitrile, or styrene, respectively, in 39–84% yields. The reaction proceeds smoothly and quickly under mild reaction conditions. The reaction can be scaled to the gram scale. A mechanism for this reaction is proposed.

Key words

Meerwein reaction - arenediazonium salts - radicals - selenium - ⁷⁷Se NMR

Publication History

Received: 05 August 2024

Accepted after revision: 18 September 2024

Article published online:
10 October 2024

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