Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2015, Issue 2, Pages 395-400Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201403355
Keywords
Nitrogen heterocycles; C-H activation; Iridium; Regioselectivity; Amidation
Categories
Funding
- National Natural Science Foundation of China (NSFC) [21302200]
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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.
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