从含氮有机化合物：酰胺、苯胺和磺胺中机械化学生产联苯

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-08-12 DOI:10.1039/d5qo01041a

Satenik Mkrtchyan, Gabriela Addová, Juraj Filo, Khurshid Ayub, Michael G Garcia, Spartak Spiridonovich Khutsishvili, Yevhen Karpun, Elena Kupcová, Vishal B. Purohit, Sehrish Sarfaraz, Mohanad Shkoor, Barbora Benicka, Oleksandr Shalimov, Vitaliy Yepishev, Jiří Zapletal, Viktor Iaroshenko

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引用次数: 0

摘要

C(sp2) -NH2在药物构建块中的存在引发了对C(sp2) -NH2运动的脱胺功能化的发现和开发的迫切需求，从而为复杂分子的后期功能化提供新的途径。在这项工作中，我们揭示了C(sp2) -NH2的机械化学脱氨芳基化，通过C(sp2) -NH2与四氟硼酸pyryium的选择性缩合，将C(sp2) -NH2原位转化为活性吡啶盐。苯胺、酰胺和磺胺的脱胺偶联是选择性功能化过程的关键发展，使前体联苯化合物的生产具有发展生物活性分子的潜力。

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Mechanochemical Production of Biphenyls from Nitrogen-Containing Organic Compounds: Amides, Anilines, and Sulfonamides

The presence of C(sp2)–NH2 in pharmaceutical building blocks provokes a pressing demand for the discovery and development of deaminative functionalization of the C(sp2)–NH2 moeity to enable new routes for late-stage functionalization of complex molecules. In this work, we disclose a mechanochemical deaminative arylation of C(sp2)–NH2 by in situ conversion of C(sp2)–NH2 to reactive pyridinium salts via selective condensation of C(sp2)–NH2 with pyrylium tetrafluoroborate. Deaminative coupling of anilines, amides, and sulfonamide represents a key development for the selective functionalization process, enabling production of precursor biphenyl compounds with the potential to develop biologically active molecules.

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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.