1612872-75-9

Upstream product

• 70-55-3 toluene-4-sulfonamide 
• 131880-76-7 1-(2-methyl-2,3-dihydro-indol-1-yl)-ethanone 
• 563-63-3 silver(I) acetate 
• 64-19-7 acetic acid 
• 6872-06-6 2-methyl indoline 
• 941-55-9 4-toluenesulfonyl azide 

Relevant academic research and scientific papers

Method for preparing N-arylsulfonamide from indoline and arylsulfonamide

The invention discloses a method for preparing N-arylsulfonamide from indoline and arylsulfonamide, belonging to the technical field of C-H bond activation and functionalization catalyzed by a transition metal. The method includes adding 1-acetyl indoline

Rhodium(III)-catalyzed direct C-7 sulfonamidation and amination of indolines with arylsulfonamides and trifluoroacetamide

A rhodium-catalyzed direct C–H sulfonamidation and amidation of C-7 position of indolines by simple and commercially available arylsulfonamides and trifluoroacetamide has been developed, affording a series of N-arylsulfonamides and N-aryltrifluoroacetamides in moderate to excellent yields, respectively. Notably, this catalytic system is highly convenient on mmol scale.

IrIII-catalyzed direct C-7 amidation of indolines with sulfonyl, acyl, and aryl azides at room temperature

A general procedure for an IrIII-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 N2 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.

Iridium(III)-catalyzed direct C-7 amination of indolines with organic azides

Iridium-catalyzed regioselective C-7 amination of indolines has been achieved with organic azides as a facile nitrogen source. The developed procedure is convenient to perform even at room temperature and applicable to a wide range of substrates with high catalytic activity. Various types of organic azides (sulfonyl, aryl, and alkyl derivatives) were all successfully reacted under the present conditions as the viable reactant. Furthermore, indoline substrates bearing easily removable N-protecting groups such as N-Boc or N-Cbz could readily be employed, highlighting the synthetic utility of this methodology. (Chemical equation presented).

Ruthenium-catalyzed C7 amidation of indoline C-H bonds with sulfonyl azides

A ruthenium-catalyzed direct C7 amidation of indoline C-H bonds with sulfonyl azides was developed. This procedure allows the synthesis of a variety of 7-amino-substituted indolines, which are useful in pharmaceutical. The good functional tolerances, as well as the mild conditions, are prominent feature of this method.