Photo-induced Substitutive Introduction of the Aldoxime Functional Group to Carbon Chains: A Formal Formylation of Non-Acidic C(sp3)−H Bonds
S. Kamijo, G. Takao, K. Kamijo, M. Hirota, K. Tao, T. Murafuji
Angew. Chem. Int. Ed., 2016, 55,9695 –9699
DOI : 10.1002/anie.201603810

Abstract: A photo-induced substitutive introduction of an aldoxime functional group to carbon chains was achieved using photo-excited 4-benzoylpyridine as a C(sp3)−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(sp3)−H bonds in a single step.