Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 19, Issue 18, Pages 4107-4117Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1ob00358e
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Funding
- Research Corporation for Science Advancement for a Cottrell College Science Award [23248]
- University of West Florida (UWF)
- UWF's Office of Research and Sponsored Programs
- NIH through the Institute of General Medical Sciences of the National Institutes of Health [1T34GM110517-01]
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This study introduces a new environmentally benign iodine-mediated strategy for synthesizing benzo[b]thiophene derivatives in a one-pot reaction process. The method allows for the synthesis of a diverse range of complex structures in high yields, with potential applications in biomedical and organic electronic fields.
In this study, a new environmentally benign iodine-mediated one-pot iodocyclization/alkylation strategy for the synthesis of benzo[b]thiophene derivatives starting from 2-alkynylthioanisoles was developed. The synthesis of a diverse population of 2,3-disubstituted benzo[b]thiophenes was achieved in high yields by employing moderate reaction conditions using 1,3-dicarbonyl substrates as the nucleophile and various substituted propargyl alcohols as both the cyclization precursor and the alkylating agent. This method resulted in the formation of a series of complex structures obtained in a single step. Additionally, a strategy was devised for the one pot iodocyclization/oxidation of propargyl alcohols into carbonyl functionalized benzo[b]thiophene structures. These green one-pot reaction processes were designed to reduce wastes and byproducts while generating a complex substitution pattern on the benzo[b]thiophene structure. The reported methodologies may be used to synthesize more functionalized benzo[b]thiophene structures that can be used in both biomedical and organic electronic applications.
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