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Issue 4, 2019
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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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Article information


Submitted
20 Nov 2018
Accepted
05 Dec 2018
First published
06 Dec 2018

Chem. Commun., 2019,55, 458-461
Article type
Communication

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, 55, 458
DOI: 10.1039/C8CC09229J

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