6533b837fe1ef96bd12a2a37
RESEARCH PRODUCT
Iodocyclization of 2-Methylthiophenylacetylenes to 3-Iodobenzothiophenes and their coupling Reactions under More Sustainable Conditions
Raffaella MancusoMelania LettieriRomina StrangisPatrizio RussoAntonio Palumbo PiccionelloSara De AngelisBartolo Gabrielesubject
Organic Chemistrycross-couplingSettore CHIM/06 - Chimica Organicaalkynesiodocyclizationsulfur heterocyclesdeep eutectic solventsdescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2022-09-16 |