(Indol-3-yl)(DMIX)Iodonium Salts: Novel Electrophilic Indole Reagents

Abstract

A new umpolung approach to the C 3 −H functionalization of indoles with diverse nucleophiles based on the intermediate formation of I(III) reagents is described. The 3,5-dimethylisoxazol-4yl auxiliary allows for selective indole transfer under catalyst-free conditions, which was impossible using previously reported reagents.Combining the mildness of transition-metal-free conditions and the high reactivity of hypervalent iodine reagents, this protocol tolerates various functional groups and provides access to indoles that are difficult to prepare conventionally.

Arylation of Diethyl Acetamidomalonate with Diaryliodonium Salts En Route to α-Arylglycines

“…In continuation of our recent studies on arylation using diaryliodonium salts, we have addressed the limitations mentioned above and developed a general and efficient method for chemoselective C-arylation of DEAM using diaryliodonium salts as the arylating agent under mild, catalyst-free conditions that are perfectly compatible with a wide range of functional groups. In addition, using aryl iodides or unsubstituted arenes, whichever is more readily available and reactive, as starting materials for the synthesis of diaryliodonium salts significantly enhances the potential of this approach compared to previously reported methods.…”