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Cascade Process from Anilines to Indoles Involving a Copper-Catalyzed Arylation
Y. Chen, X. Xie, D. Ma*
Fudan University, Shanghai and Shanghai Institute of Organic Chemistry, P. R. of China
23 January 2008 (online)
Reported is a Cu-mediated coupling of 2-halotrifluoroacetanilides with β-keto esters, followed by an acidic hydrolysis to generate 2,3-disubstituted indoles. The yields are generally good, and a variety of substituted anilines and β-keto esters survive the reaction conditions. Both 2-iodoanilides and 2-bromoanilides can be used although, as may be expected from mechanistic considerations, the reaction was observed to be more sluggish with the latter, thus requiring higher reaction temperatures.