期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 141, 期 38, 页码 15450-15455出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b08634
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资金
- Australian Research Council [FL170100041, CE140100012]
- Australian Research Council [FL170100041] Funding Source: Australian Research Council
Bench- and air-stable 1-methoxy-2,2,6,6-tetra-methylpiperidine (TEMPO-Me) is relatively unreactive at ambient temperature in the absence of an electrochemical stimulus. In this report, we demonstrate that the one-electron electrochemical oxidation of TEMPO-Me produces a powerful electrophilic methylating agent in situ. Our computational and experimental studies are consistent with methylation proceeding via a S(N)2 mechanism, with a strength comparable to the trimethyloxonium cation. A protocol is developed for the electrochemical methylation of aromatic acids using TEMPO-Me.
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