We report on a novel reaction protocol for the coupling of arenes with alkynes (the Fujiwara reaction), yielding products of formal trans-hydroarylation of the triple bond. The protocol makes use of a chelating N-heterocyclic dicarbene palladium(II) complex as catalyst and allows us to perform the reaction in a few hours with only 0.1 mol% catalyst yielding the trans-hydroarylation product in high yields and with excellent selectivity. We discuss the applicability of this reaction protocol, which appears at present quite general with respect to the alkyne, albeit limited to electron-rich arenes. We also present the results of catalyst optimisation with respect to the nature of the nitrogen substituents in the carbene units, of the bridging group between the carbene units and of the coordinated anionic ligands. Finally, we also discuss the catalytic performance of a related chelating dicarbene complex of platinum(II).

Highly efficient alkyne hydroarylation with chelating dicarbene palladium(II) and platinum(II) complexes

BIFFIS, ANDREA;TUBARO, CRISTINA;BUSCEMI, GABRIELLA;BASATO, MARINO
2008

Abstract

We report on a novel reaction protocol for the coupling of arenes with alkynes (the Fujiwara reaction), yielding products of formal trans-hydroarylation of the triple bond. The protocol makes use of a chelating N-heterocyclic dicarbene palladium(II) complex as catalyst and allows us to perform the reaction in a few hours with only 0.1 mol% catalyst yielding the trans-hydroarylation product in high yields and with excellent selectivity. We discuss the applicability of this reaction protocol, which appears at present quite general with respect to the alkyne, albeit limited to electron-rich arenes. We also present the results of catalyst optimisation with respect to the nature of the nitrogen substituents in the carbene units, of the bridging group between the carbene units and of the coordinated anionic ligands. Finally, we also discuss the catalytic performance of a related chelating dicarbene complex of platinum(II).
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11577/2449638
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