Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 361, Issue 24, Pages 5709-5714Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201901058
Keywords
benzothiophenes; sulfur heterocycles; sulfur; cross-dehydrogenative coupling; C-H functionalization
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Funding
- China Scholarship Council [201808610096]
- Foundation for Young Scholars of Shaanxi University of Science and Technology [BJ12-26]
- NSF [CAREER CHE-1650766]
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Benzothiophenes represent a pivotal class of sulfur heterocycles and their synthesis has attracted significant attention to generate bioactive scaffolds. Herein, we report a convergent, atom- and step-economic method for the synthesis benzothiophenes by cross-dehydrogenative coupling (CDC) of 4-arylthiocoumarins in good to excellent yields. We further demonstrate cross-dehydrogenative coupling of 4-arylthio-2-pyrones to afford alternative substitution of benzothiophenes. The presence of a labile ester carbonyl moiety provides functional handle for further functionalization by coumarin deconstruction. Most crucially, the manuscript demonstrates that the use of readily accessible templated synthesis has a significant potential for the rapid assembly of sulfur heterocycles by dehydrogenative coupling mechanism.
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