Decatungstate Catalyzed Photochemical Acetylation of C(sp<sup>3</sup>)–H Bonds
Qinglong Liu, Yuzhen Ding, Yuxi Gao, Yunhong Yang, Lijuan Gao, Zhiqiang Pan, Chengfeng Xia
Abstract
A direct acetylation of inert C(sp3)–H bonds was developed that was catalyzed by decatungstate under visible light irradiation and was followed by radical addition–disassociation with phenylsulfonyl ethanone oxime. The reaction displays site-selectivity in multiple C(sp3)–H bonds without prefunctionalization and directing groups. Various functional groups are well-tolerated and natural molecules are structurally feasible. CF3-modified phenylsulfonyl ethanone oxime was discovered to be necessary for enhancing the electrophilicity of imine and lowering the C–S bond cleavage energy.
Topics & Concepts
ChemistryCatalysisAcetylationPhotochemistryMedicinal chemistryOrganic chemistryBiochemistryGeneCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsOxidative Organic Chemistry Reactions