Progress towards metal-free radical alkylations of quinones under mild conditions |
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Authors: | Jordan D Galloway Ryan D Baxter |
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Institution: | Department of Chemistry & Chemical Biology, University of California, Merced, 5200 N. Lake Road, Merced, CA, 95343, USA |
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Abstract: | A new method for the radical alkylation of quinones is reported. Lewis basic nitrogen additives increase the efficacy of quinone alkylations from carboxylic acids using catalytic AgNO3 and Selectfluor as a mild oxidant. Electrochemical data suggests that certain Lewis basic additives are capable of directly reducing Selectfluor through a single-electron transfer, presumably via a charge-transfer complex. This process yields intermediates capable of promoting oxidative decarboxylation of alkyl carboxylic acids without an added metal initiator. Using this strategy, we have demonstrated progress towards a metal-free C–H quinone alkylation reaction that proceeds at room temperature under mild conditions. |
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Keywords: | Corresponding author Radical Quinones Alkylation Metal-free |
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