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Synfacts 2008(7): 0686-0686  
DOI: 10.1055/s-2008-1078472
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Indolines via C-H Activation of N-tert-Butyl-2-bromoanilines

Contributor(s): Victor Snieckus, Jignesh J. Patel
T. Watanabe, S. Oishi, N. Fujii*, H. Ohno*
Kyoto University, Japan
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Publication History

Publication Date:
20 June 2008 (online)

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Significance

Reported here is a straightforward route for the synthesis of indolines from N-alkyl-2-bromoaniline derivatives by palladium-catalyzed sp3 C-H activation of the tethered alkyl group on aniline followed by intramolecular cyclization. Combination of ligand PCy3·HBF4 with Cs2CO3 as base with Pd(OAc)2 and pivalic acid as an additive was found to be the best combination for this process. Anilines bearing EDG as well as EWG afforded the corresponding indolines in high yields.