In this paper, we describe the silver triflate/p-toluensulfonic acid co-catalysed synthesis of seventeen isocoumarins and two thieno[2,3-c]pyran-7-ones starting from 2-alkynylbenzoates and 3-alkynylthiophene-2-carboxylates, respectively. The reactions proceed with absolute regioselectivity under mild reaction conditions and low catalyst loading, to give the desired products in good to excellent yields. A conceivable reaction mechanism is proposed and supported by isotope-exchange tests, and 1H NMR studies and ad-hoc experiments.
Silver Triflate/p-TSA Co-Catalysed Synthesis of 3-Substituted Isocoumarins from 2-Alkynylbenzoates / J. Gianni, V. Pirovano, G. Abbiati. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - 16:17(2018 May 07), pp. 3213-3219. [10.1039/C8OB00436F]
Silver Triflate/p-TSA Co-Catalysed Synthesis of 3-Substituted Isocoumarins from 2-Alkynylbenzoates
J. GianniPrimo
;V. PirovanoSecondo
;G. Abbiati
Ultimo
2018
Abstract
In this paper, we describe the silver triflate/p-toluensulfonic acid co-catalysed synthesis of seventeen isocoumarins and two thieno[2,3-c]pyran-7-ones starting from 2-alkynylbenzoates and 3-alkynylthiophene-2-carboxylates, respectively. The reactions proceed with absolute regioselectivity under mild reaction conditions and low catalyst loading, to give the desired products in good to excellent yields. A conceivable reaction mechanism is proposed and supported by isotope-exchange tests, and 1H NMR studies and ad-hoc experiments.File | Dimensione | Formato | |
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