A Robust Three-Step Telescoped Synthesis of Electron- Deficient Amide Substituted Arylboronic Acids

IF 3.1 3区化学 Q2 CHEMISTRY, APPLIED Organic Process Research & Development Pub Date : 2011-01-14 DOI:10.1021/op100267p

Jason Zhu, Thomas M. Razler*, Zhongmin Xu, David A. Conlon, Eric W. Sortore, Alan W. Fritz, Roman Demerzhan, Jason T. Sweeney

引用次数: 8

Abstract

A robust three-step telescoped process for the preparation of electron-deficient amide-substituted arylboronic acids from readily available bromobenzoic acids has been developed. An EDC-HOBT-promoted amide formation of a bromobenzoic acid was followed by subjection of the product stream to a palladium-mediated cross-coupling with B₂(pin)₂. The resultant mixture of the arylboronate ester and arylboronic acid was directly treated with NaIO₄, followed by a heptane?MeTHF crystallization, to cleanly afford the corresponding arylboronic acid in good yield. This general procedure was used to synthesize electron-deficient amide-substituted arylboronic acids with a diverse array of electron-withdrawing substituents.

Abstract Image

查看原文

微信好友朋友圈 QQ好友复制链接

本刊更多论文

三步法合成缺乏电子酰胺取代芳基硼酸的研究

提出了一种以溴苯甲酸为原料制备缺电子酰胺取代芳基硼酸的三步缩合工艺。edc - hobt促进溴苯甲酸酰胺的形成，随后产物流与钯介导的B2(pin)2交叉偶联。合成的芳香硼酸酯和芳香硼酸的混合物直接用NaIO4处理，然后用庚烷?甲基苯丙胺结晶，以清洁提供相应的芳硼酸，收率高。该程序用于合成具有多种吸电子取代基的缺电子酰胺取代芳基硼酸。

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分钟内获得全文去求助

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.