Palladium/DABCO-Catalyzed Cross-Coupling Reaction And Cerium Salt-Catalyzed Organic Reactions

Palladium-catalyzed Suzuki-Miyaura cross-coupling reaction of organoboron with organic electrophiles has been recognized as one of the most important carbon-carbon bond building reactions. The contents of this dissertation mainly include: (i) the use of tertiary amines as ligand for palladium-catalyzed cross-coupling reaction; (ii) development of green chemistry of the palladium-catalyzed cross-coupling reaction; (iii) Lewis acid-catalyzed Friedel-Crafts alkylation reaction and hydration reaction of alkynes.1. An inexpensive and highly efficient Pd(OAc)2/DABC0 catalytic system has been developed for the Suzuki-Miyaura cross-coupling of aryl halides with arylboronic acids. A combination of Pd(0Ac)2 and DABCO (triethylenediamine) was observed to form an excellent catalytic system, which affords high TONs (turnover numbers, up to 950000 TONs for the reaction of Phi and p-chlorophenylboronic acid) for Suzuki-Miyaura cross-coupling of various aryl iodides and bromides with arylboronic acids. Furthermore, the reaction was carried out smoothly under aerobic conditions.2. PEG (Polyethylene glycol, an alternative green solvent to traditional organic solvents) was found as a cheap and effective reaction medium for the Pd(OAc)2/DABCO-catalyzed Suzuki Cross-Coupling reactions, which is a homogeneous system during reaction. Both the reaction media and the catalyst could be recovered for several times without loss of catalytic reactivity. The results...