Journal
GREEN CHEMISTRY
Volume 18, Issue 7, Pages 2222-2230Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5gc02626a
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Funding
- National Natural Science Foundation of China [21272021, 21472011]
- National Key Technology RD Program [2011BAD23B01]
- US National Science Foundation [OISE-0968399]
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Efficient electrochemical amino-oxygenation of styrenes has been developed for the synthesis of 3-methoxyindolines and 3-ethoxyindoline, using a simple beaker-type undivided cell with n-Bu4NI serving as a redox catalyst under constant current electrolysis (CCE) conditions. The chemistry proceeds in a paired electrolysis mode, avoiding the utilization of external oxidants and bases and therefore represents an environmentally benign means. The process also works in the absence of an additional conducting salt. Gram-scale reaction further demonstrates the practicability of the protocol. Proton NMR spectroscopy was used to demonstrate that the amino-oxygenation of N-(2-vinylphenyl) sulfonamides likely involves the initial iodoamination of the alkene, followed by nucleophilic substitution of the methoxide/ethoxide generated at the cathode.
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