Visible-Light-Driven Iron-Catalyzed Intermolecular Benzylic C(sp<sup>3</sup>)–H Amination with 1,2,3,4-Tetrazoles
Yan Du, Jingjing Tang, Yarong Wang, Junhao Hu, Changhua Chen, Zhonggui Xiong, Yang Li, Jiangli Fan, Ming Bao, Xiaoqiang Yu
Abstract
)-H amination of diphenylmethane derivatives with 1,2,3,4-tetrazoles under mild conditions has been developed. The reaction proceeds with photosensitizer-free conditions and features satisfactory to good yields. Mechanistic studies revealed that the reaction proceeded via an iron-nitrene intermediate, and H atom abstraction was the rate-determining step. Computational studies showed that the denitrogenation of 1,2,3,4-tetrazole depends on the conversion of the sextet ground state of 1,2,3,4-tetrazole-bounding iron species to the quartet spin state under visible-light irradiation.
Topics & Concepts
ChemistryNitreneTetrazoleAminationCatalysisPhotochemistryIntermolecular forceDiphenylmethaneVisible spectrumGround stateMedicinal chemistryMoleculeStereochemistryOrganic chemistryQuantum mechanicsPhysicsOptoelectronicsSynthesis and Catalytic ReactionsRadical Photochemical ReactionsCatalytic C–H Functionalization Methods