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Synthesis of indolines

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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.


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.