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Amines as Ligands Promoted Palladium Catalyzed Cross-Coupling Reactions

Author: ZhangXuDong
Tutor: LiJinHeng
School: Hunan Normal University
Course: Organic Chemistry
Keywords: Palladium Ligand Cross-coupling reaction Catalytic efficiency
CLC: O643.32
Type: Master's thesis
Year: 2006
Downloads: 199
Quote: 1
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Abstract


Palladium-catalyzed Sonogashira cross-coupling reactions of terminal alkynes with aryl halides and Suzuki-Miyaura cross-coupling reaction of aryl halides with organoboronic acids have been recognized as the important methods for the formation of carbon-carbon bonds. The contents of this dissertation mainly include the use of nitrogen-containing compounds such as amines and pyrimidines as ligands for the palladium catalyzed cross-coupling reactions.1. An inexpensive and highly efficient Pd（OAc）2/DABCO catalytic system has been developed for the Sonogashira couplings between aryl halides and terminal alkynes. A combination of Pd（OAc）2 and DABCO （triethylenediamine） was observed to form an excellent catalytic system, which affords high TONs （turnover numbers, up to 720000 TONs for the reaction of p-nitroiodophen and phenylacetylene） for the Sonogashira cross-couplings of aryl iodides and terminal alkynes.2. An efficient and copper-free Sonogashira cross-coupling reaction catalyzed by the Pd（OAc）2/pyrimidines catalytic system has been described. Aryl iodides and the activated aryl bromine coupled with terminal alkynes were conducted smoothly in moderate to excellent yields using Pd（OAc）2 and 2-aminopyrimidine-4,6-diol as the catalytic system.3. 2-Aminopyrimidine-4,6-diol was found as a stable and efficientligand for the Suzuki-Miyaura cross-couplings of aryl halides with arylboronic acids. In the presence of 3 mol % of Pd（OAc）2 and 6 mol % of 2-aminopyrimidine-4,6-diol, a variety of ArX （X = I, Br, and Cl） were coupled with arylboronic acids efficiently to offer the corresponding desired products in moderate to excellent yields. Moreover, high TONs （turnover numbers, TONs up to 1 000 000 for the reaction of iodobenzene with phenylboronic acid） for the palladium-catalyzed Suzuki-Miyaura cross-couplings were observed

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CLC: > Mathematical sciences and chemical > Chemistry > Physical Chemistry ( theoretical chemistry ),chemical physics > Chemical kinetics,catalysis > Catalytic > Catalytic reaction
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