Synthesis, characterization, and microwave-assisted catalytic activity in Heck, Suzuki, Sonogashira, and Buchwald--Hartwig cross-coupling reactions of novel benzimidazole salts bearing N-phthalimidoethyl and benzyl moieties

Authors : Hasan KÜÇÜKBAY, Ülkü YILMAZ, Kemal YAVUZ, Nesrin BUĞDAY

Pages : 1265-1278

View : 23 | Download : 9

Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :Five novel benzimidazole salts insert ignore into journalissuearticles values(\textbf{1}--\textbf{5}); having N-phthalimidoethyl and 4-substituted benzyl were synthesized and identified by $^{1}$H NMR, $^{13}$C NMR, and IR spectroscopic methods and microanalysis. A mixture of the benzimidazole salts insert ignore into journalissuearticles values(\textbf{1}--\textbf{5});, Pdinsert ignore into journalissuearticles values(OAc);$_{2}$, and K$_{2}$CO$_{3}$ in DMF-H$_{2}$O catalyzed, in high yield, the Suzuki--Miyaura and the Heck--Mizoroki cross-coupling reactions assisted by microwave irradiation in 5 min. The novel benzimidazole salts insert ignore into journalissuearticles values(\textbf{1}--\textbf{5});, Pdinsert ignore into journalissuearticles values(OAc);$_{2}$, Cs$_{2}$CO$_{3}$, PEG, and Cu nanoparticles catalyzed, in high yield, the Sonogashira coupling reaction promoted by microwave irradiation in 10 min. The same benzimidazole salts insert ignore into journalissuearticles values(\textbf{1}--\textbf{5});, Pdinsert ignore into journalissuearticles values(OAc);$_{2}$, Cs$_{2}$CO$_{3}$, and TBAB catalyzed, in moderate or low yield, the Buchwald--Hartwig reaction assisted by microwave irradiation in 60 min. The efficiency of the catalyst system in these four reactions was discussed as well as the electron-releasing and withdrawing substituent effects on the benzimidazole ligands.
Keywords : Heck Mizoroki coupling, Suzuki Miyaura coupling, Sonogashira coupling, Buchwald Hartwig coupling, benzimidazole derivatives, catalyzes, N heterocyclic carbene, microwave