Methodology to Control the Regioselective Installation of a Carboxylic Acid for the Synthesis of 2,3-Diarylpropionic Acids

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2024-10-10 DOI:10.1002/adsc.202400952

Mason Hamilton, Trina M. Perrone, Brian Popp

引用次数: 0

Abstract

A stepwise copper-catalyzed boracarboxylation then palladium-catalyzed Suzuki-Miyaura cross-coupling methodology was developed to access 2,3-diarylpropionic acid derivatives regioselectively by pre-setting the position of the carboxylic acid in the boracarboxylation reaction. This method provides access to a wide range of aryl and heteroaryl products in up to 80% isolated yield. Pharmaceutical potential was demonstrated by synthesizing a glucagon receptor antagonist drug in 3-steps (31% overall yield) from commercially available 4-tert-butylstyrene.

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控制羧酸区域选择性安装以合成 2,3-二芳基丙酸的方法学

通过预先设定硼羧化反应中羧酸的位置，开发出了一种先铜催化硼羧化、再钯催化铃木-宫浦交叉偶联的方法，可选择性地获得 2,3-二芳基丙酸衍生物。这种方法可以获得多种芳基和杂芳基产品，分离收率高达 80%。通过利用市售的 4-叔丁基苯乙烯分三步合成一种胰高血糖素受体拮抗剂药物（总收率为 31%），证明了该方法的制药潜力。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.