Three-Component Syntheses of Functionalized Selenocyanates

Yurii V. Ostapiuk; Oksana V. Barabash; Mary Y. Ostapiuk; Colin Herzberger; Mattes Plieth; Andreas Schmidt

doi:10.1055/s-0040-1720145

Synthesis, Table of Contents

Synthesis 2025; 57(03): 647-658
DOI: 10.1055/s-0040-1720145

paper

Three-Component Syntheses of Functionalized Selenocyanates

Yurii V. Ostapiuk∗

^aDepartment of Organic Chemistry, Ivan Franko National University of Lviv, Kyryla i Mefodiya Str. 6, 79005 Lviv, Ukraine

,

Oksana V. Barabash

^aDepartment of Organic Chemistry, Ivan Franko National University of Lviv, Kyryla i Mefodiya Str. 6, 79005 Lviv, Ukraine

,

Mary Y. Ostapiuk

^aDepartment of Organic Chemistry, Ivan Franko National University of Lviv, Kyryla i Mefodiya Str. 6, 79005 Lviv, Ukraine

,

Colin Herzberger

^bInstitute of Organic Chemistry, Clausthal University of Technology, Leibnizstrasse 6, 38678 Clausthal-Zellerfeld, Germany

,

Mattes Plieth

^bInstitute of Organic Chemistry, Clausthal University of Technology, Leibnizstrasse 6, 38678 Clausthal-Zellerfeld, Germany

,

Andreas Schmidt ∗

^bInstitute of Organic Chemistry, Clausthal University of Technology, Leibnizstrasse 6, 38678 Clausthal-Zellerfeld, Germany

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Abstract

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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

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References

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