Copper‐Catalyzed Three‐Component Carboazidation of Alkenes with Acetonitrile and Sodium Azide

2017/06/26 by Ala Bunescu, Tu M. Ha, Qian Wang +1 · 3 citations
Chemistry · #Catalytic C–H Functionalization Methods #Radical Photochemical Reactions #Synthesis and Catalytic Reactions

paper · doi:10.1002/ange.201705353

openalex publication_date 2017/06/26 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/28

Abstract

Abstract A copper‐catalyzed three‐component reaction of alkenes, acetonitrile, and sodium azide afforded γ‐azido alkyl nitriles by formation of one C(sp 3 )−C(sp 3 ) bond and one C(sp 3 )−N bond. The transformation allows concomitant introduction of two highly versatile groups (CN and N 3 ) across the double bond. A sequence involving the copper‐mediated generation of a cyanomethyl radical and its subsequent addition to an alkene, and a C(sp 3 )−N bond formation accounted for the reaction outcome. The resulting γ‐azido alkyl nitrile can be easily converted into 1,4‐diamines, γ‐amino nitriles, γ‐azido esters, and γ‐lactams of significant synthetic value.

Cited by

• Dual Photoredox/Copper Catalysis for the Remote C(sp3)−H Functionalization of Alcohols and Alkyl Halides by N‐Alkoxypyridinium Salts
• Copper‐Catalyzed 1,2‐Methoxy Methoxycarbonylation of Alkenes with Methyl Formate
• Zhu Jieping [wikipedia]

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