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Palladium-Catalyzed Alkenyl C–H Activation/Diamination toward Tetrahydrocarbazole and Analogs Using Hydroxylamines as Single-Nitrogen Sources

Lingbo Han, Tingjie Liu, Han Wang, Xinjun Luan

2022Organic Letters13 citationsDOI

Abstract

A palladium-catalyzed alkenyl C-H activation/diamination reaction of cycloalkenyl bromoarenes with hydroxylamines is described. A wide range of tetrahydrocarbazoles and analogs has been prepared using fine-tuning bifunctional secondary hydroxylamines as the single-nitrogen sources. Mechanistic investigations suggest that the selective alkenyl C-H activation/diamination cascade process should build the N-heterocycles.

Topics & Concepts

ChemistryPalladiumBifunctionalCatalysisAminationCascadeCombinatorial chemistryNitrogenOrganic chemistryChromatographyCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsSulfur-Based Synthesis Techniques