Direct catalytic photodecarboxylative amination of carboxylic acids with diazirines for divergent access to nitrogen-containing compounds

IF 7.9 2区 综合性期刊 Q1 CHEMISTRY, MULTIDISCIPLINARY Cell Reports Physical Science Pub Date : 2024-07-12 DOI:10.1016/j.xcrp.2024.102103
Vishala Maharaj, Paresh R. Athawale, Preeti P. Chandrachud, Justin M. Lopchuk
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Abstract

Amines, hydrazines, and nitrogen-containing heterocycles are pivotal species in medicine, agriculture, fine chemicals, and materials. Diazirines have been recently reported to serve as versatile electrophilic amination reagents for the synthesis of building blocks or late-stage C–N bond formation. Here, we report the catalytic photodecarboxylative amination of carboxylic acids with diazirines under mild conditions. The substrate scope includes broad functional group tolerance, such as ketones, esters, olefins, and alcohols, along with the late-stage amination of naproxen, ibuprofen, gemfibrozil, and gibberellic acid. Synthetic applications leverage the versatility of the intermediate diaziridines and include the regioselective preparation of a suite of 1H-indazoles, 2H-indazoles, and fluoroquinolones.

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直接催化羧酸与重氮吖啶的光解羧基胺化反应,以获得不同的含氮化合物
胺、肼和含氮杂环化合物是医药、农业、精细化工和材料领域中的关键物种。最近有报道称,重氮氨酸可作为多功能亲电氨基化试剂,用于合成构件或后期 C-N 键的形成。在此,我们报告了在温和条件下用重氮吖嗪催化羧酸的光解羧基胺化反应。底物范围包括广泛的官能团耐受性,如酮、酯、烯烃和醇,以及萘普生、布洛芬、吉非罗齐和赤霉素的后期胺化。合成应用充分利用了中间体二氮杂环胺的多功能性,包括区域选择性制备一系列 1H-吲唑、2H-吲唑和氟喹诺酮类化合物。
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来源期刊
Cell Reports Physical Science
Cell Reports Physical Science Energy-Energy (all)
CiteScore
11.40
自引率
2.20%
发文量
388
审稿时长
62 days
期刊介绍: Cell Reports Physical Science, a premium open-access journal from Cell Press, features high-quality, cutting-edge research spanning the physical sciences. It serves as an open forum fostering collaboration among physical scientists while championing open science principles. Published works must signify significant advancements in fundamental insight or technological applications within fields such as chemistry, physics, materials science, energy science, engineering, and related interdisciplinary studies. In addition to longer articles, the journal considers impactful short-form reports and short reviews covering recent literature in emerging fields. Continually adapting to the evolving open science landscape, the journal reviews its policies to align with community consensus and best practices.
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