Work

Dual Photoredox/Copper Catalysis for the Remote C(sp 3 )−H Functionalization of Alcohols and Alkyl Halides by N ‐Alkoxypyridinium Salts

Year: 2018

Type: article

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.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.201813356

Authors: Xu Bao, Qian Wang, Jieping Zhu

Institution: École Polytechnique Fédérale de Lausanne

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: École Polytechnique Fédérale de Lausanne, Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung

Award: G3181471470