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Issue 35, 2007
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Pd(II) complexes of N,S-heterocyclic carbenes with pendant and coordinated allyl function and their Suzuki coupling activities

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Abstract

3-(2-Propenyl)benzothiazolium bromide (A) provides a direct and simple entry to Pd(II) complexes with N,S-heterocyclic carbene (NSHC) ligands functionalized with an allyl pendant with hemilabile potential. Addition of salt A to Pd(OAc)2 eliminates HOAc and affords the bis(carbene) complexes cis-[PdBr2(NHSC)2] (cis-1, NSHC = 3-(2-propenyl)benzothiazolin-2-ylidene) and trans-[PdBr2(NHSC)2] (trans-1) along with the monocarbene complexes [PdBr2(NSHC)] (2) and trans-[PdBr2(benzothiazole-κN)(NSHC)] (3) as minor side products. Salt-metathesis of cis-1 with AgO2CCF3 yields the mixed dicarboxylato-bis(carbene) complex cis-[Pd(O2CCF3)2(NSHC)2] (4). Complexes cis-1, trans-1 and 4 were characterized by multinuclear NMR spectroscopies, ESI mass spectrometry and elemental analysis. The molecular structures of complexes cis-1, 2 and 3 have been determined by X-ray single crystal diffraction. Complexes cis-1 and 4 as well as an in situ mixture of Pd(OAc)2 and salt A are active toward Suzuki–Miyaura coupling of aryl bromides and activated aryl chlorides giving good conversions.

Graphical abstract: Pd(ii) complexes of N,S-heterocyclic carbenes with pendant and coordinated allyl function and their Suzuki coupling activities

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Publication details

The article was received on 08 May 2007, accepted on 25 Jun 2007 and first published on 27 Jul 2007


Article type: Paper
DOI: 10.1039/B706968E
Dalton Trans., 2007, 3952-3958

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    Pd(II) complexes of N,S-heterocyclic carbenes with pendant and coordinated allyl function and their Suzuki coupling activities

    S. K. Yen, L. L. Koh, H. V. Huynh and T. S. A. Hor, Dalton Trans., 2007, 3952
    DOI: 10.1039/B706968E

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