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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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Supplementary files

Article information


Submitted
08 May 2007
Accepted
25 Jun 2007
First published
27 Jul 2007

Dalton Trans., 2007, 3952-3958
Article type
Paper

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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