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. Gianni
Primo
;
V. Pirovano
Secondo
;
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.
isocoumarins, alkynes, silver, cyclization, mechanistic studies, pyran-2-one
Settore CHIM/06 - Chimica Organica
   PIANO DI SOSTEGNO ALLA RICERCA 2015-2017 - LINEA 2 "DOTAZIONE ANNUALE PER ATTIVITA' ISTITUZIONALE"
   UNIVERSITA' DEGLI STUDI DI MILANO
7-mag-2018
26-mar-2018
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/566744
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