Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 72, Issue 15, Pages 5574-5580Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo0703552
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A novel, three-step method of trifluoromethylation of azines via oxidative nucleophilic substitution of hydrogen in the heteroaromatic ring by a CF3- carbanion is presented. The key reaction of this process is the addition of the CF3- carbanion, generated by treatment of Me3SiCF3 with KF(s) and Ph3SnF catalyst, to N-alkylazinium salts. The resulting dihydroazines containing a trifluoromethyl group are relatively stable compounds and can be isolated in a pure form. Deprotection of the N-p-methoxybenzyl substituent and aromatization of the heterocyclic ring upon treatment with CAN provides azines with a CF3 group in the ring position originally occupied by hydrogen. The whole process can be thus considered as a nucleophilic oxidative displacement of hydrogen by a CF3- carbanion.
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