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2005
Indole derivatives
R 0140
Palladium-Catalyzed Synthesis of N-Aryl-2-benzylindolines via Tandem Arylaof 2-Allylaniline: Control of Selectivity Through in situ Catalyst Modifica12- 123 tion
tion. — The synthesis of N-aryl-2-benzylindoline derivatives via a palladium-catalyzed tandem N-arylation/cyclization/C-arylation reaction between 2-allylaniline and
two aryl halides is developed. The transformation leads to the formation of two C-N
bonds and one C-C bond in an one-pot process. A variety of electron-neutral and electron-deficient aryl bromides and heterocyclic substrates afford the corresponding benzylindolines in high yields. The selective addition of two different aryl bromides is
achieved by a key in situ modification of the catalyst such that a bulky, electron-rich,
monodentate ligand, which facilitates N-arylation, is exchanged with a chelating ligand
that promotes olefin insertion of the intermediate palladium(aryl)amid complex in preference to C-N bond-forming reductive elimination. — (LIRA, R.; WOLFE*, J. P.;
J. Am. Chem. Soc. 126 (2004) 43, 13906-13907; Dep. Chem., Univ. Mich., Ann
Arbor, MI 48109, USA; Eng.) — Bartels
2005
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