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 ofthe 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

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

Mancuso R.
;
Lettieri M.;Strangis R.;Russo P.;De Angelis S.;Gabriele B.
2022

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 ofthe 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
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/20.500.11770/339289
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