Green synthesis of benzo[b]thiophenes via iron(III) mediated 5-endo-dig iodocyclization of 2-alkynylthioanisoles
2016
Kesharwani, Tanay | Kornman, Cory T. | Tonnaer, Amanda L. | Royappa, Andrew D.
A reaction of iron(III) chloride with sodium iodide was used to generate iodine for an innovative take on electrophilic cyclization. With ethanol as solvent, the reaction was observed to provide ideal conditions for iodocyclization of 2-alkynylthioanisoles. The fundamental step allows formation of iodine which becomes free to undergo reaction with the starting alkyne to yield the cyclized product. Implementing environmentally benign and simple chemistry, 2-iodosubstituted benzo[b]thiophenes were synthesized in high yields to produce an interesting display of useful molecules.
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