School of Marine Science and Technology, Harbin Institute of Technology, Weihai 264209, P. R. China.
Org Biomol Chem. 2019 May 15;17(19):4789-4800. doi: 10.1039/c9ob00526a.
An unexpected time-controlled highly selective C3- or C2-sulfinylation of pyrroles with sulfinamides is reported for the first time. The sulfinylation of indoles with sulfinamides using this protocol is oxidant-free and can be performed under obviously more feasible conditions (1.2 equiv. of indoles, 10 min) in comparison with the precedent procedure (3-20 equiv. of indoles, 16-18 h, ammonium persulfate as oxidant, hv). A variety of functional groups were tolerated, and various C2-thioindoles and C2/3-thiopyrroles were obtained in moderate to excellent yields.
首次报道了一种意想不到的、时间控制的、对吡咯的高选择性 C3-或 C2-亚磺酰化反应，其中使用亚磺酰胺。与前序方法（3-20 当量吲哚，16-18 小时，过硫酸铵为氧化剂，hv）相比，该协议中吲哚与亚磺酰胺的亚磺酰化反应无需氧化剂，并且可以在明显更可行的条件下进行（1.2 当量吲哚，10 分钟）。各种功能基团都可以耐受，并且以中等至优异的产率得到了各种 C2-硫吲哚和 C2/3-硫吡咯。
