Switchable Copper-Catalyzed Approach to Benzodithiole, Benzothiaselenole, and Dibenzodithiocine Skeletons
Meng‐Qiao Huang, Tuanjie Li, Jian‐Quan Liu, Andrey Shatskiy, Markus D. Kärkäs, Xiang‐Shan Wang
Abstract
A copper-catalyzed reaction between 2-bromo-benzothioamides and S8 or Se involving sulfur rearrangement is reported, enabling access to benzodithioles 2 and benzothiaselenoles 6 in the presence of Cs2CO3. In the absence of S8 or Se, the reaction affords dibenzodithiocines 7 via two consecutive C(sp2)–S Ullmann couplings.
Topics & Concepts
ChemistryCopperCatalysisSulfurCombinatorial chemistryMedicinal chemistryOrganic chemistrySulfur-Based Synthesis TechniquesOrganoselenium and organotellurium chemistryChemical Synthesis and Reactions