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Solvent-controlled selective synthesis of a trans-configured benzimidazoline-2-ylidene palladium(II) complex and investigations of its Heck-type catalytic activity

2005; Elsevier BV; Volume: 690; Issue: 16 Linguagem: Inglês

10.1016/j.jorganchem.2005.04.053

1872-8561

Han Vinh Huynh, Joanne Hui Hui Ho, Tiong Cheng Neo, Lip Lin Koh,

Synthetic Organic Chemistry Methods

Reaction of N,N′-dimethylbenzimidazolyl iodide (A) with Pd(OAc)2 in DMSO gives selectively trans-bis(N,N′-dimethylbenzimidazoline-2-ylidene) palladium(II) diiodide (trans-2) in 77% yield. The selective formation of the trans-coordination isomer and thus the cis–trans rearrangement is driven by the insolubility of trans-2 in DMSO. X-ray single-crystal diffraction analysis and 13C NMR spectroscopy confirm the trans-geometry of the square planar Pd(II) complex. Catalytic studies show that cis-1 and trans-2 are highly efficient in the Mizoroki–Heck coupling reaction of aryl bromides and activated aryl chlorides both in DMF and [N(n-C4H9)4]Br as ionic liquid. The catalytic activities of Pd(II) complexes with N-heterocyclic carbene ligands derived from benzimidazole are comparable to their imidazole-derived analogues.