TFPN-Mediated Acyl Fluoride Platform: Efficient Synthesis of Esters, Thioesters, and Macrolactones from Carboxylic Acids with Diverse Nucleophiles

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-05-31 DOI:10.1039/d5qo00651a

Dou Zhang, Peng Shen, Yao Zhang, Qiuyi Zheng, Jiahui Zhang, Chunyu Han, Silin Xu, Jinhua Yang

引用次数: 0

Abstract

A TFPN (3,4,5,6-tetrafluorophthalonitrile)-mediated esterification strategy has been developed for the efficient synthesis of esters, thioesters, and macrolactones within remarkably short reaction times. Key to this approach is the utilization of in situ-generated acyl fluo-rides as transient intermediates, which circumvent stability limitations associated with conventional activated species. This method demonstrates exceptional functional group tolerance across structurally diverse substrates, including chiral molecules with complete stereochemical preservation. Notably, medium-sized macrolactones are constructed with efficiency through this protocol. Operationally simple and scalable, this platform exhibits practical versatility in late-stage functionalization of bioactive molecules, bioconjugation, and polymer chemistry, underscoring its broad synthetic utility.

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tfpn介导的酰基氟化平台：由羧酸和各种亲核试剂高效合成酯、硫酯和大内酯

一种TFPN（3,4,5,6-四氟眼腈）介导的酯化策略在非常短的反应时间内有效地合成酯、硫酯和大内酯。这种方法的关键是利用现场生成的酰基氟基作为瞬态中间体，这规避了与传统活性物质相关的稳定性限制。该方法在结构多样的底物上表现出特殊的官能团耐受性，包括具有完整立体化学保存的手性分子。值得注意的是，通过该方案可以高效地构建中等大小的内酯。该平台操作简单，可扩展，在生物活性分子、生物偶联和聚合物化学的后期功能化中展示了实用的多功能性，强调了其广泛的合成用途。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.