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Issue 19, 2013
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Expanded ring diaminocarbene palladium complexes: synthesis, structure, and Suzuki–Miyaura cross-coupling of heteroaryl chlorides in water

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Abstract

A series of new 6- and 7-membered N-heterocyclic carbene (NHC) complexes of palladium (NHC)Pd(cinn)Cl (cinn = cinnamyl = 3-phenylallyl) were synthesized and characterized structurally in the solid state. The influence of ring size (5, 6 or 7) and bulkiness of N-aryl substituents (Mes = 2,4,6-trimethylphenyl, or Dipp = 2,6-diisopropylphenyl) in carbenes on palladium catalysed Suzuki–Miyaura cross-coupling was revealed. Due to the unique stereoelectronic properties of expanded ring NHCs, a versatile, highly efficient green protocol of coupling of heteroaromatic chlorides and bromides with boronic acids has been developed. High quantitative yields of biaryls were achieved with water as solvent, under air, using low catalyst and phase transfer agent loadings, and with mild and environmentally benign base NaHCO3.

Graphical abstract: Expanded ring diaminocarbene palladium complexes: synthesis, structure, and Suzuki–Miyaura cross-coupling of heteroaryl chlorides in water

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Publication details

The article was received on 28 Nov 2012, accepted on 19 Feb 2013 and first published on 19 Feb 2013


Article type: Paper
DOI: 10.1039/C3DT32860K
Dalton Trans., 2013,42, 6859-6866

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    Expanded ring diaminocarbene palladium complexes: synthesis, structure, and Suzuki–Miyaura cross-coupling of heteroaryl chlorides in water

    E. L. Kolychev, A. F. Asachenko, P. B. Dzhevakov, A. A. Bush, V. V. Shuntikov, V. N. Khrustalev and M. S. Nechaev, Dalton Trans., 2013, 42, 6859
    DOI: 10.1039/C3DT32860K

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