Abstract
Sonogashira-Hagihara and Buchwald-Hartwig cross-coupling reactions with sydnone and sydnone imine derived catalysts
Highlights
Lücke, A.-L. et al.The Sonogashira-Hagihara[1,2,3] and Buchwald-Hartwig[4,5,6] cross-couplings are widely applied reactions in organic synthesis
Triphenylamine was prepared in almost quantitative yields, when cat. 2 was applied. It is as effective as an expanded-ring N-heterocyclic carbenes (NHC) for the synthesis of 20 46 and imidazolylidene Pd complexes for the synthesis of 20 47 and 21.46 Compound 22 was prepared in better yields when Pd(OAc)[2], NaOtBu, tBuP3 in o-xylene was used.[48]
We demonstrated that the catalysts derived from sydnones and sydnone imines can efficiently be applied in Sonogashira-Hagihara cross-couplings
Summary
A.-L. et al.The Sonogashira-Hagihara[1,2,3] and Buchwald-Hartwig[4,5,6] cross-couplings are widely applied reactions in organic synthesis. In parallel to the remarkable carrier of N-heterocyclic carbenes, NHC-palladium catalyzed Sonogashira-Hagihara cross-couplings have been reported.[8] Early reports deal with di(imidazol-1-yl-2-ylidene)methane,9 2-(imidazol-1-yl-2-ylidene)methyl)pyridine[10] and bis(1,3-di-Ntert-butylimidazol-2-ylidene) Pd complexes[11] as catalysts. We reported on Suzuki-Miyaura reactions under basic conditions as well as in acid employing sydnones as co-catalysts.[32,33,34] We report here on sydnones as catalysts or co-catalysts of Sonogashira-Hagihara and of Buchwald-Hartwig cross-coupling reactions.
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