6533b853fe1ef96bd12ad514

RESEARCH PRODUCT

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

Anne-katrin BachonTill Opatz

subject

DeprotonationPrimary (chemistry)010405 organic chemistryChemistryIntramolecular forceOrganic ChemistryHalidechemistry.chemical_element010402 general chemistry01 natural sciencesMedicinal chemistryCopper0104 chemical sciences

description

The α-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.

https://doi.org/10.1021/acs.joc.5b02659