Journal
TETRAHEDRON
Volume 72, Issue 29, Pages 4239-4244Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2016.05.062
Keywords
Deep eutectic solvents; Heterocyclization; iodocyclization; Alkynyl thiols; Thiophenes
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Funding
- MIUR PON RC [PON01_00878]
- Interuniversities Consortium C.I.N.M.P.I.S. (Bari)
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The heterocyclodehydration and iodocyclization of readily available 1-mercapto-3-yn-2-ols has been performed in a deep eutectic solvent (DES), that is, ChCl/Gly (1:2 molar ratio; ChCl=choline chloride, Gly=glycerol), as a non-conventional green solvent. The processes, carried out at 50 degrees C for 8 h in the presence of the PdI2/KI catalytic system or at room temperature for 5 h with 1.2 equiv of I-2, led to the formation of the corresponding thiophenes and 3-iodothiophenes in good to high yields. The DES/catalytic system could be easily recycled several times without appreciable loss of activity, after extraction of the thiophene product with hexane or Et2O. The alkynylation reaction of alpha-mercapto ketones, necessary for the preparation of the allcynylthiol substrates, was also successfully accomplished in the above protic eutectic mixture competitively with protonolysis. (C) 2016 Elsevier Ltd. All rights reserved.
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