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Isocyanoalkenes: Occurrence, Syntheses, and Reactivity
Journal article   Peer reviewed

Isocyanoalkenes: Occurrence, Syntheses, and Reactivity

Huan Tian and Fraser F. Fleming
Synthesis (Stuttgart), v 19
08 Sep 2025
DOI: https://doi.org/10.1055/a-2677-6462
Featured in Collection :   UN Sustainable Development Goals @ Drexel

Abstract

Isocyanoalkenes Synthesis Reactivity Additions Heterocycles
Isocyanoalkenes are a largely underexplored subset of isocyanides whose natural occurrence, synthesis, and reactivity are elucidated in this review. The discussion begins with an overview of the biosynthesis and natural occurrence, which provides a valuable context for the synthetic approaches to these unusual π-substituted alkenes. Building on this foundation, the review explores the characteristic reactivity of isocyanoalkenes, which is shaped by the strong electron-withdrawing nature of the isocyanide group and an almost complete lack of π-conjugation. Two primary modes of reactivity are highlighted: conjugate additions – especially in systems containing additional electron-withdrawing substituents – and radical additions to the isocyanide, often followed by annulation via iminyl radical intermediates. Special attention is given to two particularly versatile isocyanoalkenes – β-dimethylaminoisocyanoacetates and β-bromoisocyanoacetates – which readily undergo nucleophilic addition–elimination–cyclization sequences to efficiently assemble nitrogen-containing heterocycles. Overall, this review underscores the synthetic potential of isocyanoalkenes and highlights their emerging value in the construction of diverse heterocyclic scaffolds.

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Web of Science research areas
Chemistry, Organic
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