We report the first example of iodocyclization of readily available 2-methylthiophenylacetylenes in a deep eutectic solvent (ChCl/urea 1/2, mol/mol) as recyclable and more sustainable solvent with respect to the classical VOCs employed so far. The process successfully afforded a variety of 3-iodobenzothiophenes in good to high yields starting from differently substituted substrates, with the possibility to recycle the DES several times without appreciable lowering of the product yield. The 3-iodothiophenes thus synthesized are known to be important precursors of biologically active molecules and functionalized heterocycles, and were successfully employed for performing representative Sonogashira and Suzuki cross-coupling reactions. The solvent-catalyst system could be conveniently recycled several times without any loss of activity in both coupling processes, thus further demonstrating the practical usefulness of our approach.

Mancuso, R., Lettieri, M., Strangis, R., Russo, P., Palumbo Piccionello, A., De Angelis, S., et al. (2022). Iodocyclization of 2-Methylthiophenylacetylenes to 3-Iodobenzothiophenes and their coupling Reactions under More Sustainable Conditions. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 11(9), 1-13 [10.1002/ajoc.202200353].

Iodocyclization of 2-Methylthiophenylacetylenes to 3-Iodobenzothiophenes and their coupling Reactions under More Sustainable Conditions

Palumbo Piccionello, A
Methodology
;
2022-09-16

Abstract

We report the first example of iodocyclization of readily available 2-methylthiophenylacetylenes in a deep eutectic solvent (ChCl/urea 1/2, mol/mol) as recyclable and more sustainable solvent with respect to the classical VOCs employed so far. The process successfully afforded a variety of 3-iodobenzothiophenes in good to high yields starting from differently substituted substrates, with the possibility to recycle the DES several times without appreciable lowering of the product yield. The 3-iodothiophenes thus synthesized are known to be important precursors of biologically active molecules and functionalized heterocycles, and were successfully employed for performing representative Sonogashira and Suzuki cross-coupling reactions. The solvent-catalyst system could be conveniently recycled several times without any loss of activity in both coupling processes, thus further demonstrating the practical usefulness of our approach.
Settore CHIM/06 - Chimica Organica
https://onlinelibrary.wiley.com/doi/10.1002/ajoc.202200353
Mancuso, R., Lettieri, M., Strangis, R., Russo, P., Palumbo Piccionello, A., De Angelis, S., et al. (2022). Iodocyclization of 2-Methylthiophenylacetylenes to 3-Iodobenzothiophenes and their coupling Reactions under More Sustainable Conditions. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 11(9), 1-13 [10.1002/ajoc.202200353].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10447/578565
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