Iodine and ammonium persulfate mediated activation of DMSO: an approach to N-formylation of amides and synthesis of isatins

An efficient strategy towards N-formylation of amides and oxidation of indolines to isatins is described. This method employs readily available (NH4)(2)S2O8, I-2, and DMSO. The given method features operational simplicity, excellent functional group tolerance, broad substrate scope, and fast kinetics. Moreover, the method was applied to the synthesis of the natural product alatamide. Notably, DMSO plays three vital roles: a formyl group source, an oxidant, and a solvent.

Automated summary

An efficient strategy for N-formylation of amides and oxidation of indolines to isatins using readily available reagents has been described. This method exhibits operational simplicity, excellent functional group tolerance, broad substrate scope, and fast kinetics. Furthermore, it has been successfully applied to the synthesis of the natural product alatamide. Notably, DMSO plays three important roles as a formyl group source, an oxidant, and a solvent.