Silver triflate/p-TSA co-catalysed synthesis of 3-substituted isocoumarins from 2-alkynylbenzoates.

Title Silver triflate/p-TSA co-catalysed synthesis of 3-substituted isocoumarins from 2-alkynylbenzoates.
Authors J. Gianni; V. Pirovano; G. Abbiati
Journal Org Biomol Chem
DOI 10.1039/c8ob00436f
Abstract

In this paper, we describe the silver triflate/p-toluenesulfonic 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 reaction proceeds with absolute regioselectivity under mild reaction conditions and low catalyst loading, to afford the desired products in good to excellent yields. A conceivable reaction mechanism is proposed and supported by isotope-exchange tests, 1H NMR studies and ad hoc experiments.

Citation J. Gianni; V. Pirovano; G. Abbiati.Silver triflate/p-TSA co-catalysed synthesis of 3-substituted isocoumarins from 2-alkynylbenzoates.. Org Biomol Chem. 2018. doi:10.1039/c8ob00436f

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