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Synthesis 2023; 55(01): 131-140
DOI: 10.1055/a-1914-0423
paper

Synthesis of 3-Aryl- and 3-Alkynylbenzofurans in the Presence of a Supported Palladium Catalyst

Enikő Nagy
a   Department of Organic Chemistry, Research Group of Organic Synthesis and Catalysis, Center of Natural Sciences, University of Pannonia, Egyetem u. 10, 8200 Veszprém, Hungary
,
Zoltán Nagymihály
b   Department of Inorganic Chemistry and ELKH-PTE Research Group for Selective Chemical Syntheses, University of Pécs, Ifjúság u. 6, 7624 Pécs, Hungary
,
László Kollár
b   Department of Inorganic Chemistry and ELKH-PTE Research Group for Selective Chemical Syntheses, University of Pécs, Ifjúság u. 6, 7624 Pécs, Hungary
c   Szentágothai Research Centre, 7624 Pécs, Hungary
,
Máté Fonyó 
a   Department of Organic Chemistry, Research Group of Organic Synthesis and Catalysis, Center of Natural Sciences, University of Pannonia, Egyetem u. 10, 8200 Veszprém, Hungary
,
Rita Skoda-Földes∗
a   Department of Organic Chemistry, Research Group of Organic Synthesis and Catalysis, Center of Natural Sciences, University of Pannonia, Egyetem u. 10, 8200 Veszprém, Hungary
› Author AffiliationsThis work was supported by the European Union - European Regional Development Fund (GINOP-2.3.2-15-2016-00049) and by the Ministry of Culture and Innovation of Hungary (TKP2021-NKTA-21).
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Abstract

Suzuki and Sonogashira coupling reactions of 3-iodo-2-phenylbenzofuran, leading to the corresponding 3-aryl- and 3-alkynyl derivatives, respectively, were carried out using a silica supported pyridinium ionic liquid-based heterogeneous catalyst. Under optimized reaction conditions, arylboronic acids with either electron-withdrawing or -donating substituents as well as terminal alkynes with aromatic or aliphatic groups could be coupled to the benzofuran skeleton efficiently. The application of this catalyst made it possible to carry out the reaction under phosphine-free and, in the case of the Sonogashira coupling, under copper-free conditions. The catalyst retained its activity in at least 7 subsequent runs in both types of reactions. Palladium leaching of less than 1% of the original amount used in the catalytic reaction was observed under optimized conditions in most cases. The methodology was applied successfully to the synthesis of nine different 3-aryl- and ten different 3-alkynylbenzofuran derivatives in moderate to high yields.

Key words

Suzuki coupling - Sonogashira coupling - heterogeneous palladium catalyst - 3-arylbenzofurans - 3-alkynylbenzofurans

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1914-0423.
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Publication History

Received: 10 June 2022

Accepted after revision: 01 August 2022

Accepted Manuscript online:
01 August 2022

Article published online:
28 September 2022

© 2022. Thieme. All rights reserved

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