Suzuki–Miyaura and Related Cross‐Couplings in Aqueous Solvents Catalyzed by Di(2‐pyridyl)methylamine‐Palladium Dichloride Complexes

作者: Carmen Nájera , Juan Gil-Moltó , Sofia Karlström

DOI: 10.1002/ADSC.200404195

关键词:

摘要: Di(2-pyridyl)methylamine-based palladium dichloride complexes 4 are versatile catalysts for different types of cross-coupling reactions in water or aqueous solvents under aerobic conditions. The Suzuki–Miyaura reaction arylboronic acids can be performed with bromoarenes reflux using K2CO3 as base at room temperature 60 °C methanol KOH base. For aryl chlorides the corresponding cross-couplings carried out refluxing and TBAB additive to provide biaryls heterobiaryls. Arylboronic react benzylic allylic substrates such chlorides, acetates carbonates also acetone base, give diarylmethanes arylpropenes. Trimethylboroxine alkylboronic coupled bromo- chloroarenes furnish methyl- butylarenes. These have been shorter times microwave irradiation. Several important intermediates as, 4′-methylbiphenyl-2-carbonitrile, 4-biphenylacetic acid, 3-(3-methylphenyl)benzoic 4,5-diphenyl-2-methyl-3(2H)pyridazinone 2-(4′-fluorobenzyl)thiophene prepared conditions good yields.

参考文章(58)
Jennifer C. Ma, Dennis A. Dougherty, The Cationminus signpi Interaction. Chemical Reviews. ,vol. 97, pp. 1303- 1324 ,(1997) , 10.1021/CR9603744
Sambasivarao Kotha, Kakali Lahiri, Dhurke Kashinath, Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis Tetrahedron. ,vol. 58, pp. 9633- 9695 ,(2002) , 10.1016/S0040-4020(02)01188-2
Adam F. Littke, Gregory C. Fu, Palladium-Catalyzed Coupling Reactions of Aryl Chlorides Angewandte Chemie International Edition. ,vol. 41, pp. 4176- 4211 ,(2002) , 10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO;2-U
Gang Zou, Y.Krishna Reddy, J.R. Falck, Ag(I)-promoted Suzuki–Miyaura cross-couplings of n-alkylboronic acids Tetrahedron Letters. ,vol. 42, pp. 7213- 7215 ,(2001) , 10.1016/S0040-4039(01)01536-2
Josef Silberg, Thomas Schareina, Rhett Kempe, K Wurst, Michael R Buchmeiser, N-Acyl-N,N-dipyridyl and N-acyl-N-pyridyl-N-quinoyl amine based palladium complexes. Synthesis, X-ray structures, heterogenization and use in Heck couplings Journal of Organometallic Chemistry. ,vol. 622, pp. 6- 18 ,(2001) , 10.1016/S0022-328X(00)00783-X
Matthew Gray, Ian P Andrews, David F Hook, John Kitteringham, Martyn Voyle, Practical methylation of aryl halides by Suzuki-Miyaura coupling Tetrahedron Letters. ,vol. 41, pp. 6237- 6240 ,(2000) , 10.1016/S0040-4039(00)01038-8
X. Fan, N.-J. Xu, J.-G. Shi, Bromophenols from the red alga Rhodomela confervoides. Journal of Natural Products. ,vol. 66, pp. 455- 458 ,(2003) , 10.1021/NP020528C