Exploring the oxidative cyclization of substituted N-aryl enamines: Pd-catalyzed formation of indoles from anilines

Author: Neumann, J.J.; Rakshit, S.; Droge, T.; Wurtz, S.; Glorius, F.

Description: The direct Pd-catalyzed oxidative coupling of two C-H-bonds within N-aryl-enamines 1 allows the efficient formation of differently substituted indoles 2. In this cross-dehydrogenative coupling, many different functional groups are tolerated and the starting material N-aryl-enamines 1 can be easily prepared in one step from commercially available anilines. In addition, the whole sequence can also be run in a one-pot fashion. Optimization data, mechanistic insight, substrate scope, and applications are reported in this full paper.

Subject Headings: Amines/chemistry; Aniline Compounds/chemistry; Catalysis; Cyclization; Indoles/chemical synthesis/chemistry; Molecular Structure; Oxidation-Reduction; Palladium/chemistry

Keywords: Amines/chemistry; Aniline Compounds/chemistry; Catalysis; Cyclization; Indoles/chemical synthesis/chemistry; Molecular Structure; Oxidation-Reduction; Palladium/chemistry

Publication year: 2011

Journal or book title: Chemistry (Weinheim an der Bergstrasse, Germany)

Volume: 17

Issue: 26

Pages: 7298-7303

Find the full text : https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/chem.201100631

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Type: Journal Article

Serial number: 2814