Hypervalent Iodine-mediated Benzylic C–H Amination And C5 Fluorination Of Quinolines

Hypervalent iodine compounds have excellent reactivity and metalloid activity,which are widely used in various fields of modern organic synthesis.The introduction of this paper mainly introduces the direct functionalization of C–H bond mediated by hypervalent iodine compounds,including the construction of C–N bond,C–F bond,C–C bonds,C–O bonds and so on.The main contents of this paper are the study of C–H bond functionalization reactions mediated by hypervalent iodine compounds,which are benzylic C–H amination of 4-methylacetaniline and C5 fluorination of 8-amidoquinoline.1.A hypervalent iodine remote oxidative benzylic C–H amination of 4-methylanilides with N-fluorobenzenesulfonimide(NFSI)was developed.The reaction did not require the involvement of transition metal catalysts,and the reaction conditions were mild and neutral.It had good functional group tolerance and high regioselectivity even with multi-substituted 4-methylanilides.This method provides an efficient and novel method for the construction of sp3 C–N bonds.2.A hypervalent iodine mediated C5 C–H fluorination of 8-amidoquinoline with Ag F was developed.It has good functional group tolerance and high regioselectivity for different acyl-substituted 8-amidoquinolines.This method realized C5 nucleophilic fluorination of 8-amidoquinoline mediated by hypervalent iodine compounds for the first time,which provides a new method for fluorination of this type of compounds.