Negative, the sp2 carbon (ipso carbon of phenyl triflate) would not react with amide ion via either Sn1 or Sn2 mechanism. the high reactivity of benzylic position toward substitution reaction is attributed to the stability of reaction intermediate. This reason can not stand well in this case. But it does not mean that this reaction will not go. A point that I must emphasize here is "the reaction mechanism". Phenyl triflate, in which a good leaving group is contained, "might" react with strong nucleophile under strong conditions. It undergoes SnAr mechanism. But in fact, this reaction occurs via benzyne mechanism instead of SnAr because that SnAr takes place while strong electron- withdrawing groups are contained in phenyl trilate. The simple "unactivated" phenyl trilate shows very poor activity toward SnAr. On the other hand, benzyne mechanism is a possible pathway to transfer phenyl triflate to aniline. The difficulty of the use of NaNH2 is the major problem to utilize this reaction to transfer phenyl triflate to aniline. Thus, the alternative "transition-metal-catalyzed" amination is wildly adopted to do amination. For example, Buchwald-Hartwig amination transfers aromatic halide or aromatic triflate to N-substituted aniline in the presence of palladium catalyst with moderate to high yield and relatively mild reaction conditions. ※ 引述《CsmuKoji (hiphop MUSIC ￾  ￾)》之銘言： : 可以從phenyl triflate然後加 NaNH2 : 走benzylic的反應機構 然後得 aniline嗎 : 不好意思 突然想到的 ^^" : ※ 引述《volley (生涯第一支全壘打)》之銘言： : : 我猜...先做成phenyl triflate,再用鈀催化進行Hartwig amination, : : 得到N-ethylaniline,以過量碘甲烷與之反應得到ammonium salt後 : : 進行Hoffmann elimination即可... : : 真麻煩. -- A:一顆快速直球...讓你投得既不快速又沒有尾勁,失敗... 滑球一出手,沒弧度...失敗.. 曲球不會彎曲..失敗... 指叉球又掉不下來,一投就被打全壘打~失敗中的失敗 最慘的就是打者了,根本打不到球,還被觸身!!你有沒有搞錯!!!!! 喂!!觸身咧...喂!!觸身打到我了你有沒有看到!!!!! B:叫防護員上來冰敷吧! --

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