Abstract
Reaction of the sterically bulky 1,3-dibenzhydrylbenzimidazolium bromide (Bh 2-bimyH +Br −) ( A) with Pd(OAc) 2 in DMSO yielded a mono(carbene) Pd(II) complex 1 with a N-bound benzimidazole derivative, which resulted from an unusual NHC rearrangement reaction. Reaction of A with Ag 2O, on the other hand, cleanly gave the Ag(I) carbene complex [AgBr(Bh 2-bimy)] ( 2), which has been used as a carbene-transfer agent to prepare the acetonitrile complex trans-[PdBr 2(CH 3CN)(Bh 2-bimy)] ( 3). Dissociation of acetonitrile from complex 3 and subsequent dimerization afforded the dinuclear Pd(II) complex [PdBr 2(Bh 2-bimy)] 2 ( 4) in quantitative yield. All complexes were fully characterized by multinuclear NMR spectroscopies, ESI mass spectrometry and X-ray diffraction analysis. Furthermore, the catalytic activity of complex 4 in aqueous Suzuki–Miyaura cross-coupling reactions was studied and compared with that of its previously reported less bulky analogue [PdBr 2( i Pr 2-bimy)] 2.
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