Photo‐induced Substitutive Introduction of the Aldoxime Functional Group to Carbon Chains: A Formal Formylation of Non‐Acidic C(sp3)−H Bonds. (29th June 2016)

• Record Type: Journal Article
• Authors: Kamijo, Shin; Takao, Go; Kamijo, Kaori; Hirota, Masaki; Tao, Keisuke; Murafuji, Toshihiro
• Is Part Of: Angewandte Chemie. Volume 128:Number 33(2016)
• Page Start: 9847
• Page End: 9851
• Publication Date: 2016-06-29
• Subjects: Aldoxime -- 4-Benzoylpyridin -- C-H-Funktionalisierung -- Photoreaktionen -- Radikale; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201603810
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: A photo‐induced substitutive introduction of an aldoxime functional group to carbon chains was achieved using photo‐excited 4‐benzoylpyridine as a C(sp 3 )−H bond cleaving agent and arylsulfonyl oxime as an aldoxime precursor. The non‐acidic C−H bonds in various substances, including cycloalkanes, ethers, azacycles, and cyclic sulfides, were chemoselectively converted at ambient temperature under neutral conditions. The present transformation is a formal formylation of non‐acidic C(sp 3 )−H bonds in a single step.