Cu-Catalyzed Coupling of Aryl Halides Utilizing Ammonia and Hydroxypicolinamide Ligands

IF 3.1 3区化学 Q2 CHEMISTRY, APPLIED

Organic Process Research & Development Pub Date : 2025-05-15 DOI:10.1021/acs.oprd.5c00101

David J. Bernhardson, Ian Hotham, Liam S. Sharninghausen, Robert A. Singer, Daniel W. Widlicka

引用次数: 0

Abstract

The hydroxypicolinamide family of ligands has previously demonstrated utility in Cu-catalyzed C–N couplings and hydroxylation of heteroaryl halides. The application of these ligands has been extended to the coupling of ammonia with aryl bromides and iodides using the dimethoxy picolinamide scaffold ligand. By tailoring reaction conditions, Cu-DMPS provides high reactivity and selectivity toward amination over hydroxylation. Utilizing aqueous ammonia or anhydrous ammonia with K₃PO₄ in MeOH provides robust conversion of bromides and iodides to the corresponding aryl amines. Additionally, this catalytic system gives efficient C–N couplings with simple primary amines by using the same general reaction conditions.

Abstract Image

查看原文本刊更多论文

利用氨和羟基喹啉酰胺配体铜催化芳基卤化物的偶联

羟基喹啉酰胺家族的配体已经在cu催化的C-N偶联和杂芳基卤化物的羟基化中得到证实。这些配体的应用已经扩展到使用二甲氧基吡啶酰胺支架配体将氨与芳基溴化物和碘化物偶联。通过调整反应条件，Cu-DMPS提供高反应活性和选择性胺化羟基化。在MeOH中使用含K3PO4的水氨或无水氨，可将溴化物和碘化物转化为相应的芳基胺。此外，该催化体系在相同的一般反应条件下与简单伯胺进行了高效的C-N偶联。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Organic Process Research & Development 化学-应用化学

CiteScore

6.90

自引率

14.70%

发文量

251

审稿时长

2 months

期刊介绍： The journal Organic Process Research & Development serves as a communication tool between industrial chemists and chemists working in universities and research institutes. As such, it reports original work from the broad field of industrial process chemistry but also presents academic results that are relevant, or potentially relevant, to industrial applications. Process chemistry is the science that enables the safe, environmentally benign and ultimately economical manufacturing of organic compounds that are required in larger amounts to help address the needs of society. Consequently, the Journal encompasses every aspect of organic chemistry, including all aspects of catalysis, synthetic methodology development and synthetic strategy exploration, but also includes aspects from analytical and solid-state chemistry and chemical engineering, such as work-up tools，process safety, or flow-chemistry. The goal of development and optimization of chemical reactions and processes is their transfer to a larger scale; original work describing such studies and the actual implementation on scale is highly relevant to the journal. However, studies on new developments from either industry, research institutes or academia that have not yet been demonstrated on scale, but where an industrial utility can be expected and where the study has addressed important prerequisites for a scale-up and has given confidence into the reliability and practicality of the chemistry, also serve the mission of OPR&D as a communication tool between the different contributors to the field.