Synthesis and reactivity of N-trifluoromethyl-N-nitrosotrifluoromethanesulfonamide as a new type of trifluoromethylating agent.
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概要
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<I>N</I>-Trifluoromethyl-<I>N</I>-nitrosotrifluoromethanesulfonamide (TNS-Tf) was synthesized in a 58% yield by the reaction of trifluoronitrosomethane with hydroxylamine followed by the treatment with trifluoromethanesulfonyl fluoride in the presence of a base. TNS-Tf was demonstrated to be an effective trifluoromethylating agent photochemically or thermally for aromatics, thiols, disulfides, and uridine derivatives. The insertion reaction by two trifluoromethyl groups of TNS-Tf to the sulfur-sulfur bonds was observed in the reaction with disulfides having electron-withdrawing groups, giving 2 mols of trifluoromethylthio compounds. Furthermore, TNS-Tf served as a good reagent for mild and convenient in situ generation of trifluoromethylcopper complex which converted iodoaromatics to trifluoromethyl-substituted aromatics in good yields. Similarly, <I>N</I>-trifluoromethyl-<I>N</I>-nitrosononafluoro-1-butanesulfonamide (TNS-Nf) was synthesized in a 36% yield. The examination of the reactivity indicated that this type of <I>N</I>-nitroso sulfonamides became to be sources of both perfluoroalkyl radicals contained.
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