4-羟基喹啉的n选择性二氟甲基化

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-10-08 DOI:10.1021/acs.orglett.5c03246

Sandeep Kumawat, , , Gopika N. Nair, , , Venkata Narayana Kalevaru, , , Sebastian Wohlrab, , , Taras Tarasiuk, , , Tetyana Yegorova, , , Pavel K. Mykhailiuk*, , and , Kishore Natte*,

引用次数: 0

摘要

4-羟基喹啉的N-选择性二氟甲基化是一个艰巨的挑战，由于竞争的N-和o -二氟甲基化途径。在此，我们提出了一种温和、高效、可扩展的方案，使用BrCF2CO2H和LiOtBu选择性地对4-羟基喹啉进行n -二氟甲基化。该方法可耐受反应性官能团，如羧酸、酯和酰胺。还合成了一系列n -氘二氟甲基类似物（−CF2D）。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

N-Selective Difluoromethylation of 4-Hydroxyquinolines

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N-Selective Difluoromethylation of 4-Hydroxyquinolines

N-selective difluoromethylation of 4-hydroxyquinolines is a formidable challenge due to competing N- and O-difluoromethylation pathways. Herein, we present a mild, efficient, and scalable protocol using BrCF₂CO₂H and LiO^tBu for the selective N-difluoromethylation of 4-hydroxyquinolines. This method tolerates reactive functional groups such as carboxylic acid, ester, and amide. A series of N-deuterodifluoromethyl analogues (−CF₂D) is also synthesized.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.