Inorganica Chimica Acta p. 3113 - 3121 (2010)
Update date:2022-09-26
Topics:
John, Alex
Shaikh, Mobin M.
Ghosh, Prasenjit
A series of palladium complexes, trans-[1-(R)-pz3,5-Me2]2PdCl2 {R = CH2CONH(2,6-i-Pr2-C6H3) (1b) and 2-(OH)-C6H10 (2b)}, supported over N/O-functionalized pyrazole derived ligands effectively catalyzed the more challenging Suzuki-Miyaura cross-coupling of a variety of activated aryl chlorides with phenyl boronic acid in air in a mixed-aqueous medium (DMF:H2O, v/v = 9:1) in moderate to excellent yields. Besides the commonly encountered C sp2-Csp2 coupling, the 1b and 2b precatalysts also catalyzed the relatively difficult Csp2-Csp3 coupling of benzyl chloride with phenyl boronic acid. The 1b and 2b complexes were synthesized by the direct reaction of the respective N/O-functionalized pyrazolyl ligands, 1a and 2a, with (COD)PdCl2 in 62-66% yields. The stability of the pyrazole-palladium interaction in the 1b and 2b complexes has been attributed to the deeply buried Npyrazole-Pd interaction as evidenced from the density functional theory (DFT) studies.
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