Journal
ACS CATALYSIS
Volume 7, Issue 1, Pages 380-387Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.6b02636
Keywords
gold; domino process; cyclization; Hanztsch ester; 1H-isochromene
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Funding
- Ministere de l'Education et de la Recherche
- Centre National de la Recherche Scientifique (CNRS)
- Institut de Recherches Servier
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The gold-catalyzed domino cyclization/nucleophilic reaction of ortho-carbonylalkynylaryls has been studied. Thus, 2-(pyridin-2-ylethynyl)benzaldehyde has been chosen to isolate key intermediates that may take part in the reaction mechanism. Employing Hantzsch ester (HEH) as nucleophile, it has been impossible to isolate the corresponding gold-alkenyl specie; however, when methanol was used as solvent (and nucleophile), the expected chelate gold-vinyl complex was isolated and unambiguously characterized by X-ray analysis. When HEH is present in the alcoholic reaction mixture, isotopic studies show that the cleavage of the Au-C bond of gold-vinyl complex proceeds through a proto-demetalation pathway, rather than a plausible metal-hydride reductive elimination mechanism. Finally, with the aim of broadening the scope of the cyclization/reduction reaction previously reported, we present that the catalytic system is robust and applicable for a diverse family of challenging substrates presenting ester, aldehyde, ether, alkene, and alkyne functionalities.
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