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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
A benzimidazole-based Cu(II) complex catalyzed site-selective C-H sulfenylation of imidazo-[1,2-a]pyridines using CS2
Kingkar Ghosh1, Narendra Nath Ghosh2, Prasun Choudhury1
1Department of Chemistry, University of North Bengal, Darjeeling 734013, India. debmayukh285@gmail.com.
Abstract:
A new benzimidazole-based Cu(II) complex catalyzed site-selective sulfenylation of imidazo[1,2-a]pyridines with benzyl/alkyl/allyl bromides and CS2 at 100 °C in DMF : H2O is reported. The present methodology has been developed for the synthesis of 3-sulfenyl imidazo[1,2-a]pyridines in good yields with a broad substrate scope. In this protocol, CS2, commonly known as a non-polar small molecule bioregulator (SMB), is converted to valuable sulfenylated imidazo[1,2-a]pyridine derivatives. In addition, theoretical investigations along with experimental evidence unfold the insights into the probable mechanistic pathway of site-selective sulfenylation from S,S-dibenzyltrithiocarbonate, which is particularly formed as an intermediate during the reaction.
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