Dual Photoredox/Copper Catalysis for the Remote C(sp3)−H Functionalization of Alcohols and Alkyl Halides by N‐Alkoxypyridinium Salts

2018/12/27 by Xu Bao, Qian Wang, Jieping Zhu · 1 citation
Chemistry · #Catalytic C–H Functionalization Methods #Radical Photochemical Reactions #Synthesis and Catalytic Reactions

paper · doi:10.1002/anie.201813356

openalex publication_date 2018/12/27 · openalex created_date 2019/01/11 · openalex updated_date 2026/07/17

Abstract

Abstract Under mild dual photoredox/copper catalysis, the reaction of N‐alkoxypyridinium salts with readily available silyl reagents (TMSN 3 , TMSCN, TMSNCS) afforded δ‐azido, δ‐cyano, and δ‐thiocyanato alcohols in high yields. The reaction went through a domino process involving alkoxy radical generation, 1,5‐hydrogen atom transfer (1,5‐HAT) and copper‐catalyzed functionalization of the resulting C‐centered radical. Conditions for catalytic enantioselective δ‐C(sp 3 )−H cyanation were also documented.

Citations

• Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis
• Copper-catalyzed methylative difunctionalization of alkenes
• Copper‐Catalyzed Three‐Component Carboazidation of Alkenes with Acetonitrile and Sodium Azide

Cited by

• Zhu Jieping [wikipedia]

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