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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Title
Green synthesis of benzo[b]thiophenes via iron(III) mediated 5-endo-dig iodocyclization of 2-alkynylthioanisoles
Publication Details
Tetrahedron letters, Vol.57(3), pp.411-414
Resource Type
Journal article
Publisher
Elsevier; United Kingdom
Number of pages
4
Grant note
University of West Florida (UWF)
Research Corporation for Science Advancement
UWF's Office of Research and Sponsored Programs