Goel Nikita, Kumari Poonam, Phillips Arushi, Bhagat Sunita
Department of Chemistry, ARSD College, Dhaula Kuan, New Delhi, 110021.
Amity Insitute of Applied Science, Amity University, Noida.
Chem Rec. 2025 Aug;25(8):e202500068. doi: 10.1002/tcr.202500068. Epub 2025 Apr 24.
Organic fluorine compounds encompass a vast and diverse variety of species that possess unique biological activity due to the presence of fluorine atoms. Fluorine is highly electronegative, increases the lipophilicity (fat-solubility) and hydrophobicity (water-repellent nature) of molecules, often exhibit remarkable chemical and thermal stability. This is especially useful in drug design, as it can improve the bioavailability of pharmaceutical compounds and help them interact more effectively with biological membranes. The growing demand for fluorinated compounds in materials science, agrochemicals, and medicine has made selective fluorine incorporation into organic molecules a challenging but necessary component of modern organic synthesis. Development of C-F building blocks are invaluable in organic synthesis due to their ability to impart chemical stability, selectivity, and reactivity to organic molecules. This article provides a detailed analysis of two popular fluorination processes: deoxyfluorination and decarboxyfluorination. Deoxyfluorination is the process of enhancing the physicochemical properties of molecules by replacing hydroxyl groups with fluorine atoms. Decarboxyfluorination is a type of chemical reaction where transformation of carboxylic acid derivatives into fluorinated compounds. The various fluorinating reagents, mechanistic processes, synthetic uses and substrate scope are covered in this section. When combined, these novel transformation strategies provide effective and focused approaches to the production of C-F bonds, offering useful resources for obtaining fluorinated compounds. This review mainly focuses on the construction of fluorinated compounds via deoxygenative and decarboxylative fluorination since 2011. We hope this review offers a useful conceptual overview and inspires further advancements in the efficient construction of C-F bond.
有机氟化合物包含种类繁多、各式各样的物种,由于氟原子的存在,它们具有独特的生物活性。氟具有很强的电负性,会增加分子的亲脂性(脂溶性)和疏水性(拒水性),通常表现出卓越的化学稳定性和热稳定性。这在药物设计中特别有用,因为它可以提高药物化合物的生物利用度,并帮助它们更有效地与生物膜相互作用。材料科学、农用化学品和医学领域对含氟化合物的需求不断增长,使得将氟选择性地引入有机分子成为现代有机合成中一项具有挑战性但又必不可少的组成部分。碳氟结构单元的开发在有机合成中具有重要价值,因为它们能够赋予有机分子化学稳定性、选择性和反应活性。本文详细分析了两种常见的氟化过程:脱氧氟化和脱羧氟化。脱氧氟化是通过用氟原子取代羟基来增强分子物理化学性质的过程。脱羧氟化是一种将羧酸衍生物转化为含氟化合物的化学反应类型。本节涵盖了各种氟化试剂、反应机理、合成用途和底物范围。这些新颖的转化策略相结合,为碳氟键的生成提供了有效且有针对性的方法,为获得含氟化合物提供了有用的资源。本综述主要聚焦于自2011年以来通过脱氧氟化和脱羧氟化构建含氟化合物的研究。我们希望这篇综述能提供一个有用的概念性概述,并激发在碳氟键高效构建方面的进一步进展。