Issue 17, 2018

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

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

Supplementary files

Article information

Article type
Paper
Submitted
19 Feb 2018
Accepted
24 Mar 2018
First published
26 Mar 2018

Org. Biomol. Chem., 2018,16, 3213-3219

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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