Iida Hiroki, Demizu Ryuta, Ohkado Ryoma
Department of Chemistry, Graduate School of Natural Science and Technology , Shimane University , 1060 Nishikawatsu , Matsue 690-8504 , Japan.
J Org Chem. 2018 Oct 5;83(19):12291-12296. doi: 10.1021/acs.joc.8b01878. Epub 2018 Sep 11.
A green, aerobic sulfenylation of imidazo[1,2- a]pyridines was performed using thiols, a flavin-and-iodine dual catalytic system, and environmentally benign molecular oxygen as the only sacrificial reagent. The dual metal-free catalysts smoothly promote a unique stepwise tandem process, beginning with the aerobic oxidation of a thiol to afford a disulfide that is utilized in the oxidative sulfenylation of the imidazo[1,2- a]pyridine. This process has afforded diverse 3-sulfenylimidazo[1,2- a]pyridines of biological interest and is environmentally friendly, as benign HO is the only byproduct.
利用硫醇、黄素-碘双催化体系以及环境友好型分子氧作为唯一牺牲试剂，实现了咪唑并[1,2-a]吡啶的绿色需氧亚磺酰化反应。这两种无金属催化剂顺利地促进了一个独特的逐步串联过程，该过程始于硫醇的需氧氧化，生成一种二硫化物，该二硫化物用于咪唑并[1,2-a]吡啶的氧化亚磺酰化反应。这一过程得到了多种具有生物学意义的3-亚磺酰基咪唑并[1,2-a]吡啶，并且环境友好，因为良性的HO是唯一的副产物。
