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. 2025 Jun 6;90(22):7498-7506.
doi: 10.1021/acs.joc.4c02915. Epub 2025 May 21.

Application of the Horner-Wadsworth-Emmons Olefination in the Construction of E-α,β-Unsaturated β-Boryl Nitriles

Kaja Gosak  1   2 , Martin Črnugelj  1 , Zdenko Časar  1   3
Affiliations

Application of the Horner-Wadsworth-Emmons Olefination in the Construction of E-α,β-Unsaturated β-Boryl Nitriles

Kaja Gosak et al. J Org Chem. .

Abstract

Herein, we describe a simple transition-metal-free synthesis of E-α,β-unsaturated β-boryl nitriles by the Horner-Wadsworth-Emmons reaction starting from potassium acyltrifluoroborates. The methodology encompasses a broad range of alkyl and aryl substrates. The reaction conditions are simple, and the reaction products are in most cases isolated with good yields as pure E isomers without column chromatography.

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Figures

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1. Background and Context
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2. Scope of Horner–Wadsworth–Emmons Olefination of Acyltrifluoroborates 1
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3. Use of E-α,β-Unsaturated β-Boryl Nitriles and KAT Olefination Scope Extension
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