Synfacts 2008(2): 0133-0133  
DOI: 10.1055/s-2007-992464
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Cascade Process from Anilines to Indoles Involving a Copper-Catalyzed Arylation

Contributor(s): Victor Snieckus, Toni Rantanen
Y. Chen, X. Xie, D. Ma*
Fudan University, Shanghai and Shanghai Institute of Organic Chemistry, P. R. of China
Further Information

Publication History

Publication Date:
23 January 2008 (online)

Significance

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.