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Issue 17, 2018
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Silver triflate/p-TSA co-catalysed synthesis of 3-substituted isocoumarins from 2-alkynylbenzoates

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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.

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

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Publication details

The article was received on 19 Feb 2018, accepted on 24 Mar 2018 and first published on 26 Mar 2018


Article type: Paper
DOI: 10.1039/C8OB00436F
Citation: Org. Biomol. Chem., 2018,16, 3213-3219
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    Silver triflate/p-TSA co-catalysed synthesis of 3-substituted isocoumarins from 2-alkynylbenzoates

    J. Gianni, V. Pirovano and G. Abbiati, Org. Biomol. Chem., 2018, 16, 3213
    DOI: 10.1039/C8OB00436F

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