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Two isomeric 1,4-thiaborin derivatives fused by two thiophene rings (dithieno-1,4-thiaborins, DTTBs) were synthesized in two steps from commercially available materials, and their structures were confirmed by X-ray crystallographic analysis. DTTBs… Click to show full abstract
Two isomeric 1,4-thiaborin derivatives fused by two thiophene rings (dithieno-1,4-thiaborins, DTTBs) were synthesized in two steps from commercially available materials, and their structures were confirmed by X-ray crystallographic analysis. DTTBs 1 and 2 showed excellent stability towards air and moisture. Theoretical calculations revealed that the fusion of thiophenes enhanced the aromaticity of the centered 1,4-thiaborins compared to their corresponding dibenzothiaborins. Furthermore, DTTBs 1 and 2 could be further functionalized by metalation followed by addition of electrophile. DTTBs are promising platforms upon which it is possible to build the next generation of organoboron π-electron materials.
Journal Title: Asian Journal of Organic Chemistry
Year Published: 2017
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