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Green synthesis of benzo[b]thiophenes via iron(III) mediated 5-endo-dig iodocyclization of 2-alkynylthioanisoles
Journal article   Peer reviewed

Green synthesis of benzo[b]thiophenes via iron(III) mediated 5-endo-dig iodocyclization of 2-alkynylthioanisoles

Tanay Kesharwani, Cory T. Kornman, Amanda L. Tonnaer and Andrew D. Royappa
Tetrahedron letters, Vol.57(3), pp.411-414
01/20/2016
Web of Science ID: WOS:000369556900044

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Abstract

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. (C) 2015 Elsevier Ltd. All rights reserved.

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