Transition-metal-catalyzed C-H Carbonvlative Reaction To Access Lactams

The carbonylation reaction is an effective synthetic method for constructing carbonyl compounds,and has significant influence in industry and academic research.Since Heck and co-workers reported their pioneering work on transition-metal-catalyzed carbonylation of aryl halides,the carbonylation reaction has drawn increasing attention in the field of organic synthesis.With the development of the C-H functionalization,the C-H carbonylation reaction has also attracted the interest of researchers.The C-H carbonylation reaction has great development potential and research value by directly inserting CO into C-H bond(C(sp)-H,C(sp2)-H,C(sp3)-H)to synthesize carbonyl compounds.The first chapter of this thesis demonstrate the history of the carbonylation reaction and focus on the research progress achieved in recent years within the area of C-H carbonylation.The research work of this thesis is about transition-metal-catalyzed C-H carbonylative synthesis of lactam compounds with benzene-1,3,5-triyl triformate(TFBen,it is a solid CO source developed by our group)as the CO source.The contents are as follows:1.The second chapter demonstrate palladium-catalyzed C-H carbonylative synthesis of isoindolinones from benzylamines with TFBen as the CO source.This reaction tolerates a wide range of functional groups,affording a series of isoindolinone derivatives.2.The third chapter demonstrate cobalt-catalyzed C-H carbonylative synthesis of free(NH)-benzo[cd]indol-2(1H)-ones from naphthylamides with TFBen as the CO source.The activation of C-H bond selectively occurs at C8 position of the naphthalene ring.Various free(NH)-benzo[cd]indol-2(1H)-ones were obtained by this procedure.In addition,two BET bromodomain inhibitors have been successfully synthesized by this reaction and existing synthetic strategies.3.The fourth chapter demonstrate cobalt-catalyzed C-H carbonylative synthesis of phthalimides from N-(pyridin-2-ylmethyl)benzamides with TFBen as the CO source.This procedure has a board substrate scope and good functional-group tolerance,providing various phthalimides derivatives.