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Ir III ‐Catalyzed Direct C‐7 Amidation of Indolines with Sulfonyl, Acyl, and Aryl Azides at Room Temperature
Author(s) -
Hou Wei,
Yang Yaxi,
Ai Wen,
Wu Yunxiang,
Wang Xuan,
Zhou Bing,
Li Yuanchao
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403355
Subject(s) - chemistry , sulfonyl , amination , aryl , functional group , catalysis , reaction conditions , combinatorial chemistry , organic chemistry , polymer , alkyl
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.