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Metal-Free Intramolecular Carbocyanation of Activated Alkenes: Functionalized Nitriles Bearing β-Quaternary Carbon Centers

Authors

  • Jianming Chen,

    1. Department of Organic Chemistry, College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012 (China)
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  • Gongfeng Zou,

    1. Department of Organic Chemistry, College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012 (China)
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  • Prof. Dr. Weiwei Liao

    Corresponding author
    1. Department of Organic Chemistry, College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012 (China)
    • Department of Organic Chemistry, College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012 (China)

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  • We gratefully acknowledge financial support from the NSFC (no. 21102054) and Open Project of State Key Laboratory for Supramolecular Structure and Materials (sklssm201315).

Abstract

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The CN shuffle: The described intramolecular alkenyl- and acylcyanation reaction of activated alkenes proceed by cleavage of a C[BOND]N bond. This protocol provides access to functionalized acyclic nitriles with quaternary carbon centers under neutral and mild reaction conditions, demonstrates broad scope, and good functional-group compatibility and versatility. Y=O or CHR4; R1,R4=electron-withdrawing group; TBACN=tetrabutylammonium cyanide.

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