C-c Bond Formation Via Vinylic C-h Activation

After reviewing Pd-catalyzed Fujiwara-Moritani reactions this thesis reports several new approaches for C-C bond formation by Pd-catalysis. The reactions occur via an olefin C-H activation. The work is divided into four major sections as follows.Chapter1begins by reviewing the Pd-catalyzed C-C bond formation through olefin C-H activation, particularly the dehydrogenative Heck reactions. This chapter includes four parts:(1) coupling of arenes with olefins,(2) coupling of perfluoroarenes with olefins,(3) coupling of heteroarenes with olefins, and (4) coupling of alkenes with olefins.Chapter2deals with FeCl3·6H2O-catalyzed direct coupling of alkenes with alcohols and cross-/homo-coupling of alcohols, giving the corresponding substituted (E)-alkenes. This entry offers several advantages like mild conditions, atom efficiency, environment-friendly procedure, and high stereospecificity. In addition, the reaction can be done on a large-scale.Chapter3introduces Pd(OAc)2-catalyzed oxidative olefination of furans and thiophenes with ally] esters. The direct oxidative olefination of furans and thiophenes with electron-rich alkenes, such as allyl esters and ethers, is realized firstly under our reaction conditions.Chapter4develops the direct cross-coupling of simple alkenes with allyl esters and acrylates catalyzed by Pd(OAc)2. Various aryl-and heteroaryl-substituted ethylenes and aliphatic alkenes all can couple with allyl esters and acrylates under our reaction conditions, giving the expected1,3-dienes as the major products.Finally, a summary of Pd-catalyzed dehydrogenative Fujiwara-Moritani reactions and an outlook on these reactions in ongoing study are given.