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Electrophilic cyanation of allylic boranes: synthesis of β,γ-unsaturated nitriles containing allylic quaternary carbon centers

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Abstract

The electrophilic cyanation of allylic boranes, a process that is applicable to the construction of allylic quaternary carbon centers, is reported. The reaction has a broad substrate scope with a high functional group tolerance. The results represent an unprecedented and powerful tool for preparing synthetically useful β,γ-unsaturated nitriles, including derivatives that have been difficult to access using existing methods. The synthetic utility of the method was further demonstrated by functional group interconversions of the cyano group of the products.

Graphical abstract: Electrophilic cyanation of allylic boranes: synthesis of β,γ-unsaturated nitriles containing allylic quaternary carbon centers

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Publication details

The article was received on 20 Nov 2018, accepted on 05 Dec 2018 and first published on 06 Dec 2018


Article type: Communication
DOI: 10.1039/C8CC09229J
Citation: Chem. Commun., 2019, Advance Article
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    Electrophilic cyanation of allylic boranes: synthesis of β,γ-unsaturated nitriles containing allylic quaternary carbon centers

    K. Kiyokawa, S. Hata, S. Kainuma and S. Minakata, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C8CC09229J

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