4.7 Article

Synthesis of 1,2-Disubstituted Indoles from α-Aminonitriles and 2-Halobenzyl Halides

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 5, Pages 1858-1869

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b02659

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Funding

  1. Rhineland Palatinate Center for Natural Products Research

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The alpha-alkylation of deprotonated Strecker products derived from primary amines and aromatic aldehydes with 2-halobenzyl halides furnishes intermediates that can be cyclized to 1,2-disubstituted indoles in moderate to high yields (up to 94% over two steps) by microwave-assisted copper- or palladium-catalyzed intramolecular cross-coupling.

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