IrIII-Catalyzed Direct C-7 Amidation of Indolines with Sulfonyl, Acyl, and Aryl Azides at Room Temperature

A general procedure for an Ir-III-catalyzed C-7 selective C-H amidation and amination of indolines is reported. The reaction exhibits good functional group tolerance, requires no external oxidants, and releases N-2 as the single byproduct, thus providing an environmentally benign, readily scalable method for the synthesis of 7-aminoindolines. More importantly, acyl, sulfonyl, and aryl azides can be employed as the amino source in this C-H amidation reaction under very mild and pH-neutral reaction conditions (i. e., room temperature) to afford N-(7-indolinyl) amides, N-(7indolinyl)-sulfonamides, and N-(7-indolinyl) arylamines in good to excellent yields. In addition, a one-pot synthesis for 7-aminoindoles was developed. Overall, this procedure is robust, reliable, and compatible in air.