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Metalated isocyanides: formation, structure, and reactivity
Journal article   Peer reviewed

Metalated isocyanides: formation, structure, and reactivity

Bilal Altundas, John-Paul R Marrazzo and Fraser F Fleming
Organic & biomolecular chemistry, v 18(33), pp 6467-6482
26 Aug 2020
DOI: https://doi.org/10.1039/d0ob01340d
PMID: 32766609
Featured in Collection :   UN Sustainable Development Goals @ Drexel

Abstract

Metalated isocyanides are highly versatile organometallics. Central to the reactivity of metalated isocyanides is the presence of two orthogonally reactive carbons, a highly nucleophilic "carbanion" inductively stabilized by a carbene-like isocyanide carbon. The two reactivities are harnessed in the attack of metalated isocyanides on π-electrophiles where an initial nucleophilic attack leads to an electron pair that cyclizes onto the terminal isocyanide carbon in a rapid route to diverse, nitrogenous heterocycles. Harnessing the potent nucleophilicity of metalated isocyanides while preventing electrophilic attack on the terminal isocyanide carbon has largely been driven by empirical heuristics. This review provides a foundational understanding by surveying the formation, structure, and properties of metalated isocyanides. The focus on the interplay between the structure and reactivity of metalated isocyanides is anticipated to facilitate the development and deployment of these exceptional nucleophiles in complex bond constructions.

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23 citations in Web of Science
21 citations in Scopus

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Web of Science research areas
Chemistry, Organic
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