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Triflic Anhydride (Tf2O)-Activated Transformations of Amides, Sulfoxides and Phosphorus Oxides via Nucleophilic Trapping
Synthesis ( IF 2.2 ) Pub Date : 2021-10-27 , DOI: 10.1055/a-1679-8205 Hai Huang 1 , Jun Yong Kang 2
Synthesis ( IF 2.2 ) Pub Date : 2021-10-27 , DOI: 10.1055/a-1679-8205 Hai Huang 1 , Jun Yong Kang 2
Affiliation
Trifluoromethanesulfonic anhydride (Tf2O) is utilized as a strong electrophilic activator in a wide range of applications in synthetic organic chemistry, leading to the transient generation of a triflate intermediate. This versatile triflate intermediate undergoes nucleophilic trapping with diverse nucleophiles to yield novel compounds. In this review, we describe the features and applications of triflic anhydride in organic synthesis reported in the past decade, especially in amide, sulfoxide, and phosphorus oxide chemistry through electrophilic activation. A plausible mechanistic pathway for each important reaction is also discussed.1 Introduction2 Amide Chemistry2.1 Carbon Nucleophiles2.2 Hydrogen Nucleophiles2.3 Nitrogen Nucleophiles2.4 Oxygen and Sulfur Nucleophiles2.5 hosphorus Nucleophiles2.6 A Vilsmeier-Type Reagent2.7 Umpolung Reactivity in Amides3 Sulfoxide Chemistry3.1 Oxygen Nucleophiles3.2 Carbon Nucleophiles3.3 Nitrogen Nucleophiles3.4 Thionium Reagents4 Phosphorus Chemistry4.1 Hendrickson’s Reagent4.2 Diaryl Phosphine Oxides4.3 Phosphonates, Phosphates and Phosphinates5 Conclusion and Outlook
中文翻译:
三氟甲磺酸酐 (Tf2O)-通过亲核捕获激活酰胺、亚砜和磷氧化物的转化
三氟甲磺酸酐 (Tf2O) 在合成有机化学的广泛应用中被用作强亲电活化剂,导致三氟甲磺酸酯中间体的瞬时生成。这种多功能的三氟甲磺酸酯中间体与不同的亲核试剂进行亲核捕获以产生新的化合物。在这篇综述中,我们描述了过去十年报道的三氟甲磺酸酐在有机合成中的特征和应用,特别是通过亲电活化在酰胺、亚砜和氧化磷化学中的应用。还讨论了每个重要反应的合理机制途径。1 介绍 2 酰胺化学 2.1 碳亲核试剂 2.2 氢亲核试剂 2.3 氮亲核试剂 2.4 氧和硫亲核试剂 2.5 磷亲核试剂 2.6 一种 Vilsmeier 型试剂 2。
更新日期:2022-01-05
中文翻译:
三氟甲磺酸酐 (Tf2O)-通过亲核捕获激活酰胺、亚砜和磷氧化物的转化
三氟甲磺酸酐 (Tf2O) 在合成有机化学的广泛应用中被用作强亲电活化剂,导致三氟甲磺酸酯中间体的瞬时生成。这种多功能的三氟甲磺酸酯中间体与不同的亲核试剂进行亲核捕获以产生新的化合物。在这篇综述中,我们描述了过去十年报道的三氟甲磺酸酐在有机合成中的特征和应用,特别是通过亲电活化在酰胺、亚砜和氧化磷化学中的应用。还讨论了每个重要反应的合理机制途径。1 介绍 2 酰胺化学 2.1 碳亲核试剂 2.2 氢亲核试剂 2.3 氮亲核试剂 2.4 氧和硫亲核试剂 2.5 磷亲核试剂 2.6 一种 Vilsmeier 型试剂 2。