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Kolychev EL, Asachenko AF, Dzhevakov PB, et al. Expanded ring diaminocarbene palladium complexes: synthesis, structure, and Suzuki-Miyaura cross-coupling of heteroaryl chlorides in water. Dalton Trans. 2013;42(19):6859-66doi: 10.1039/c3dt32860k.
Kolychev, E. L., Asachenko, A. F., Dzhevakov, P. B., Bush, A. A., Shuntikov, V. V., Khrustalev, V. N., & Nechaev, M. S. (2013). Expanded ring diaminocarbene palladium complexes: synthesis, structure, and Suzuki-Miyaura cross-coupling of heteroaryl chlorides in water. Dalton transactions (Cambridge, England : 2003), 42(19), 6859-66. https://doi.org/10.1039/c3dt32860k
Kolychev, Eugene L, et al. "Expanded ring diaminocarbene palladium complexes: synthesis, structure, and Suzuki-Miyaura cross-coupling of heteroaryl chlorides in water." Dalton transactions (Cambridge, England : 2003) vol. 42,19 (2013): 6859-66. doi: https://doi.org/10.1039/c3dt32860k
Kolychev EL, Asachenko AF, Dzhevakov PB, Bush AA, Shuntikov VV, Khrustalev VN, Nechaev MS. Expanded ring diaminocarbene palladium complexes: synthesis, structure, and Suzuki-Miyaura cross-coupling of heteroaryl chlorides in water. Dalton Trans. 2013 May 21;42(19):6859-66. doi: 10.1039/c3dt32860k. PMID: 23493919.
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Dalton Trans. 2013 May 21;42(19):6859-66. doi: 10.1039/c3dt32860k.

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

Dalton transactions (Cambridge, England : 2003)

Eugene L Kolychev, Andrey F Asachenko, Pavel B Dzhevakov, Alexander A Bush, Viacheslav V Shuntikov, Victor N Khrustalev, Mikhail S Nechaev

Affiliations

  1. A.V. Topchiev Institute of Petrochemical Synthesis, RAS, Leninsky Prosp., 29, Moscow 119991, Russian Federation.

PMID: 23493919 DOI: 10.1039/c3dt32860k

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.

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