4.5 Article

Synthesis of Acrylonitriles via Mild Base Promoted Tandem Nucleophilic Substitution-Isomerization of α-Cyanohydrin Methanesulfonates

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CHINESE JOURNAL OF CHEMISTRY
卷 39, 期 4, 页码 913-917

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WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.202000579

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Acrylonitriles; Nucleophilic substitution; Isomerization; α ‐ Cyanohydrin methanesulfonates; Alkenyl boronic acids

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This study presents an efficient synthesis of acrylonitriles via a mild and transition metal-free protocol with good chemical yields for a wide range of substrates and good functional group tolerance.
Main observation and conclusion We have developed an efficient synthesis of acrylonitriles via mild base promoted tandem nucleophilic substitution-isomerization of alpha-cyanohydrin methanesulfonates with alkenylboronic acids. This transition metal-free protocol works under simple and mild conditions and offers good chemical yields for a wide range of substrates and demonstrates good functional group tolerance.

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