一种基于苯并咪唑的铜（II）配合物，以CS作为硫源，催化咪唑并[1,2 -]吡啶的位点选择性C-H硫烯基化反应。
A benzimidazole-based Cu(II) complex catalyzed site-selective C-H sulfenylation of imidazo-[1,2-]pyridines using CS as a sulfur source.
作者信息
Ghosh Kingkar, Ghosh Narendra Nath, Choudhury Prasun, Bhattacharjee Subham, Saha Rajat, Deb Mayukh, Biswas Kinkar
机构信息
Department of Chemistry, University of North Bengal, Darjeeling 734013, India.
Department of Chemistry, University of Gour Banga, Malda 732101, India.
出版信息
Org Biomol Chem. 2024 Oct 2;22(38):7791-7800. doi: 10.1039/d4ob00868e.
A new benzimidazole-based Cu(II) complex catalyzed site-selective sulfenylation of imidazo[1,2-]pyridines with benzyl/alkyl/allyl bromides and CS at 100 °C in DMF : HO is reported. The present methodology has been developed for the synthesis of 3-sulfenyl imidazo[1,2-]pyridines in good yields with a broad substrate scope. In this protocol, CS, commonly known as a non-polar small molecule bioregulator (SMB), is converted to valuable sulfenylated imidazo[1,2-]pyridine derivatives. In addition, theoretical investigations along with experimental evidence unfold the insights into the probable mechanistic pathway of site-selective sulfenylation from ,-dibenzyltrithiocarbonate, which is particularly formed as an intermediate during the reaction.
据报道，一种新型的基于苯并咪唑的铜（II）配合物在100°C下于N,N-二甲基甲酰胺（DMF）与水（HO）的混合溶剂中，催化咪唑并[1,2 - ]吡啶与苄基/烷基/烯丙基溴和二硫化碳（CS）发生位点选择性亚磺酰化反应。目前的方法已用于合成3 - 亚磺酰基咪唑并[1,2 - ]吡啶，产率良好，底物范围广泛。在该方案中，通常被称为非极性小分子生物调节剂（SMB）的二硫化碳（CS）被转化为有价值的亚磺酰化咪唑并[1,2 - ]吡啶衍生物。此外，理论研究与实验证据揭示了从α,α'-二苄基三硫代碳酸酯进行位点选择性亚磺酰化可能的反应机理途径的见解，α,α'-二苄基三硫代碳酸酯是反应过程中特别形成的中间体。
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