Soft–Hard Acid–Base‐Controlled C−H Trifluoroethoxylation and Trideuteriomethoxylation of Anilides,Asian Journal of Organic Chemistry

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Soft–Hard Acid–Base‐Controlled C−H Trifluoroethoxylation and Trideuteriomethoxylation of Anilides
Asian Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2018-03-02 , DOI: 10.1002/ajoc.201800069
Saikat Maiti ₁ , Toufique Alam ₁ , Prasenjit Mal ₁

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Phenyliodinetrifluoroacetate (PIFA)‐mediated dehydrogenative C−H etherification of anilides is reported for the synthesis of ‐OCH₂CF₃ and ‐OCD₃ incorporated aryl ethers. Nucleophilicity of the added nucleophiles and soft–hard acid–base (SHAB) principle were rationalized to understand those reactions. Anilides and PIFA led to the electrophiles either softer nitrenium ions or harder carbenium ions. The harder nucleophile alcohols exclusively reacted with the carbenium ions to produce aryl ethers.

中文翻译：

软硬酸碱控制的苯丙胺三氟乙氧基化和三氘甲氧基化

据报道，苯碘碘三氟乙酸酯（PIFA）介导的苯甲酰胺的脱氢CH-H醚化反应可合成-OCH ₂ CF ₃和-OCD ₃芳基醚。为了了解这些反应，合理化了添加亲核试剂的亲核性和软硬酸碱（SHAB）原理。苯胺和PIFA导致亲电体中的氮离子较软或碳正离子较硬。较硬的亲核醇仅与碳鎓离子反应生成芳基醚。

更新日期：2018-03-02

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