Tf2O/TTBP (2,4,6-Tri-tert-butylpyrimidine): An Alternative Amide Activation System for the Direct Transformations of Both Tertiary and Secondary Amides,The Journal of Organic Chemistry

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Tf2O/TTBP (2,4,6-Tri-tert-butylpyrimidine): An Alternative Amide Activation System for the Direct Transformations of Both Tertiary and Secondary Amides
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-09-09 , DOI: 10.1021/acs.joc.1c01572
Qian He ₁ , Jian-Liang Ye ₁ , Fang-Fang Xu ₁ , Hui Geng ₁ , Ting-Ting Chen ₁ , Hang Chen ₁ , Pei-Qiang Huang ₁

Affiliation

Ten types of Tf₂O/TTBP-mediated amide transformation reactions were investigated. The results showed that compared with pyridine derivatives 2,6-di-tert-butyl-4-methylpyridine (DTBMP) and 2-fluoropyridine (2-F-Pyr.), TTBP can serve as an alternative amide activation system for the direct transformation of both secondary and tertiary amides. For most surveyed examples, higher or comparable yields were generally obtained. In addition, Tf₂O/TTBP combination was used to promote the condensation reactions of 2-(tert-butyldimethylsilyloxy)furan (TBSOF) with both tertiary and secondary amides, the one-pot reductive Bischler–Napieralski-type reaction of tertiary lactams, and Movassaghi and Hill’s modern version of the Bischler–Napieralski reaction. The value of the Tf₂O/TTBP-based methodology was further demonstrated by the concise and high-yielding syntheses of several natural products.

中文翻译：

Tf2O/TTBP（2,4,6-三叔丁基嘧啶）：用于叔酰胺和仲酰胺直接转化的替代酰胺活化系统

研究了十种 Tf ₂ O/TTBP 介导的酰胺转化反应。结果表明，与吡啶衍生物2,6-二叔丁基-4-甲基吡啶（DTBMP）和2-氟吡啶（2-F-Pyr.）相比，TTBP可以作为直接转化的替代酰胺活化体系。二级和三级酰胺。对于大多数调查的例子，通常获得更高或相当的产量。此外，Tf ₂ O/TTBP组合用于促进2-(叔-丁基二甲基甲硅烷氧基）呋喃（TBSOF）与叔酰胺和仲酰胺，叔内酰胺的一锅还原比施勒-纳皮拉斯基反应，以及 Movassaghi 和希尔的现代版比施勒-纳皮拉斯基反应。几种天然产物的简明和高产合成进一步证明了基于Tf _{2 O/TTBP 的方法的价值。}

更新日期：2021-09-09

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