Studies On Palladium-Catalyzed Reactions In The Construction Of C-C/C-X Bonds

Chapter ?In part one,the author introduces aziridine,a kind of useful intermediate in organic synthesis.It can synthesize diamines,chiral ligands,amino acids and other bioactive compounds by reacting with various nucleophiles containing carbon,nitrogen,oxygen,sulfur,halogen,etcIn part two,the author introduces the famous Catellani reaction,and summarize the recent developments from the perspective of electrophilic reagents involved in the reaction.These electrophilic reagents include:alkyl halides,aryl halides,amine compounds,acyl compounds,epoxides/aziridines and thiol compounds.In addition,the author also summarizes four possible reaction mechanisms of Catellani reaction:Pd(?)species,a trans-metallation between two different Pd(?)centers,electrophilic substitution and SN2 nucleophilic substitutionIn part three,?-allyl palladium chemistry plays an important role in organic chemistry,and the most representative reaction is the Tsuji-Trost reaction.The author introduces the most recent advances in classic Tsuji-Trost reaction from different allyl electrophilic reagentsIn part four,palladium-catalyzed intramolecular Heck-type reaction and C-H bond activation of aryl halide with tethered alkene moieties in a domino process has been exploited as valuable and powerful tools to enable C-C and C-heteroatom bonds formation.The author summarizes the recent developments of palladium-catalyzed alkene-tethered aryl halides reactions from intramolecular and intermolecular reactions.Chapter ?The author has developed a novel strategy to synthesize indoline compounds from commercial and readily accessible aryl iodides and N-sulfonated aziridines.This process involves aziridine ring-opening followed by palladium-catalyzed coupling-cyclization,which contains Caryl-Calkyl and N-Caryl bond formation in one step.In-depth mechanistic studies and DFT calculations ruled out the Pd(?)-intermediate process,and an SN2 nucleophilic ring-opening process is likely to proceed.Chapter ?A novel strategy of palladium-catalyzed allyloxy-tethered aryl iodides reactions is reported.Allylamine derivatives had been obtained with the formation of new C-O and C-N bonds via Tsuji-Trost reaction,when allyloxy-tethered aryl iodide reacted with 1-tosylaziridine.Because of the retention of reactive functional groups(Ar-I and C=C bonds),the allylamine compounds can further produce nine-and eight-membered heterocyclic compounds via Heck reaction.In addition,an rearrangement product phenanthrenol was isolated when o-iodoaryl(2-aryl)allyl ether was introduced.