4.7 Article

Copper-catalyzed oxidative selective cyclization/C-N cross-coupling of two tryptamines to access 3a-tryptamine-pyrroloindolines

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 10, Issue 3, Pages 774-779

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo01936a

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Transition-metal-catalyzed C-N bond formation reactions have been extensively studied, but the site-selective intermolecular C-N cross-coupling between identical molecules is relatively unexplored. In this study, we present a highly selective copper-catalyzed oxidative cyclization/C-N cross-coupling of two tryptamines using O-2 as the terminal oxidant, providing a practical and direct route to a new class of indole-linked-pyrroloindoline compounds in moderate to good yields. Mechanistic studies revealed that the coordination between the copper catalyst and the tryptamine substrate is crucial for controlling chemoselectivity.
Transition-metal-catalyzed C-N bond formation reactions have been widely studied in recent decades, but site-selective intermolecular C-N cross-coupling between the carbon and nitrogen sites of two identical molecules is less explored. Herein, we report the highly selective copper-catalyzed oxidative cyclization/C-N cross-coupling of two tryptamines with O-2 as the terminal oxidant, which provides practical and direct access to a new class of indole-linked-pyrroloindoline compounds in moderate to good yields. Mechanistic studies suggested that the coordination between the copper catalyst and the tryptamine substrate is key for chemoselectivity control.

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