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Synthesis of indolines

Recent Literature

The use of N,N′-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene (SIPr) as a ligand and tBuONa as the base for sequential palladium-catalyzed intra- followed by intermolecular aryl amination enables the synthesis of N-arylated five-, six- and seven-membered nitrogen heterocycles.
R. Omar-Amrani, R. Schneider, Y. Fort, Synthesis, 2004, 2257-2534.

A Pd-catalyzed intermolecular 1,2-carboamination route to indolines from N-aryl ureas and 1,3-dienes proceeds under mild conditions in relatively nonacidic media via a C-H insertion/carbopalladation/nucleophilic displacement process. The in situ generation, or preformation of a palladium tosylate emerges as a key parameter in gaining the requisite reactivity.
C. E. Houlden, C. D. Bailey, J. G. Ford, M. R. Gagné, G. C. Lloyd-Jones, K. I. Booker-Milburn, J. Am. Chem. Soc., 2008, 130, 10066-10067.

An efficient, palladium-catalyzed reduction of N-(tert-butoxycarbonyl)indoles gives N-(tert-butoxy­carbonyl)indolines in good yields in the presence of polymethylhydrosiloxane (PMHS) as reducing agent at room temperature.
S. Chandrasekhar, D. Basu, C. R. Reddy, Synthesis, 2007, 1509-1512.