Study On The Palladium-Catalyzed Carbon-carbon Bond Coupling Reaction In Green Media

Transition-metal-catalyzed C-C bond-formation reaction is among the mostpowerful methods of organic synthesis, In recent years, it has been the research hottopic of catalytic chemistry and organic chemistry, especially in the aspects of greensynthetic methodologies. It is an important subject of green chemistry to look forenvironment-friendly reaction medium instead of traditional organic solvent. Liquidlow-molecular-weight polyethylene glycol （PEG） is of great concern by researchers asa new type of green organic reaction solvent. PEG has the advantages of non-toxic,non-volatile, non-flammable, good thermal stability, biodegradable, as well as easyrecovery and recycling. In addition, PEG can dissolve a large number of organiccompounds and organic metal complexes. Therefore, PEG as a substitute for organicsolvents and homogeneous catalyst carrier has been successfully applied to manyorganic reactions.This thesisis includes four chapters.Chapter1: The Research Progress in Carbon-Carbon Bond Cross-CouplingReactions.This chapter reviews the research progress in carbon-carbon cross-couplingreaction in recent years.Chapter2: Study on Atom-Efficient Stille Cross-Coupling Reaction Catalyzed by insitu Formed Nanoparticles from PdCl₂-PEG400SystemThe Stille coupling of tetraphenylstannane with aryl iodides and aryl bromidescatalyzed by in situ formed nanoparticles from commercial available palladiumdichloride in PEG-400under microwave irradiation is developed. The reaction wascarried out in an atom-efficient way, as4equivalents of aryl halides coupledeffectively with1equivalent of tetraphenylstannane to furnish4equivalents of thecorresponding functionalized biaryls in high yields.Chapter3: Study on Palladium Nanoparticals Catalyzed Atom-Efficient Suzuki–Miyaura Coupling Reaction.A rapid and highly efficient ligand-free Suzuki–Miyaura cross-coupling reaction between aryl bromides/iodides and sodium tetraphenylborate using the in situgenerated palladium nanoparticles from commercial available palladium dichloride inPEG-400/H₂O at50℃is developed. The reaction was carried out in an atom-efficientway, All four phenyl groups of sodium tetraphenylborate participated in the reactionand produced polyfunctional biaryls in excellent yields.Chapter4: Pd-catalyzed Heck type coupling reaction between benzenesulfonylchloride and terminal olefin compoundsPd-catalyzed Heck type coupling reaction between benzenesulfonyl chloride andterminal olefin compounds in1,4-dioxane at110℃and in the presence of PPh₃isdescribed. The corresponding products are obtained in good yields.