Silver triflate/p-TSA co-catalysed synthesis of 3-substituted isocoumarins from 2-alkynylbenzoates
Jonathan Gianni1, Valentina Pirovano, Giorgio Abbiati
1Dipartimento di Scienze Farmaceutiche, Sezione di Chimica Generale e Organica "Alessandro Marchesini", Università degli Studi di Milano, Via Venezian, 21, 20133 Milano, Italy. giorgio.abbiati@unimi.it.
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.
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