Journal
ORGANIC LETTERS
Volume 24, Issue 18, Pages 3358-3362Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c01059
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This study reports a safe and convenient copper-catalyzed selective oxidation method using atmospheric oxygen as the oxidant. The method allows for the oxidative rearrangement of indole compounds, leading to the formation of various functionalized products. This represents a significant advance in the field of indole oxidation.
ABSTRACT: We report a safe and convenient open-flask coppercatalyzed selective oxidation/functionalization methodology for tetrahydrocarbolines and tetrahydro-fi-carbolines that employs atmospheric O2 as the terminal oxidant. The system is applicable to oxidative rearrangement of tetrahydro-fi-carbolines, tetrahydrocarboline oxidation to a-alkoxy carbazoles and spirooxindoles, and Witkop oxidation. Mechanistic experiments indicated that a singleelectron oxidation process is responsible for the tunable selectivity control. This copper-catalysis protocol represents a significant advance in the field of indole oxidation.
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