Silver-Catalyzed Domino Hydroarylation/Cycloisomerization Reactions of ortho-Alkynylbenzaldehydes: An Entry to Functionalized Isochromene Derivatives
| Autor: | Véronique Michelet, Patrick Y. Toullec, Gaëlle Mariaule, Gregory John Robert Newsome, Philippe Belmont |
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| Rok vydání: | 2014 |
| Předmět: |
Mesylates
Reaction conditions Molecular Structure Chemistry Organic Chemistry Biochemistry Medicinal chemistry Catalysis Domino Benzaldehyde chemistry.chemical_compound Cycloisomerization Cyclization Alkynes Benzaldehydes Moiety Organic chemistry Benzopyrans Physical and Theoretical Chemistry Trifluoromethanesulfonate |
| Zdroj: | Organic Letters. 16:4570-4573 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol5021256 |
| Popis: | A Ag-catalyzed versatile and efficient access to 1H,1-arylisochromenes is reported. Starting from ortho-alkynylbenzaldehydes bearing various substitution patterns on the benzaldehyde and alkynyl units, the use of silver triflate (10 mol %) allowed a domino hydroarylation/cycloisomerization reaction process, leading to aryl-functionalized 1H-isochromene (>10 compounds, 80–98% yields). Notably, the reaction conditions were also compatible with benzaldehydes bearing an aliphatic-substituted alkynyl moiety with modest to good yields (34–88%, 10 compounds). |
| Databáze: | OpenAIRE |
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