Palladium‐Catalyzed Heck‐Matsuda Reaction of Morita‐Baylis‐Hillman Alcohols with Aryl Triazenes: Unexpected Role of Nitric Acid as the Promoter

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry Pub Date : 2025-03-24 DOI:10.1002/ejoc.202401386

Yue Shen , Mengni Pan , Daming Liu , Hui You , Xinying He , Yang Li , Prof. Dr. Chaoren Shen , Dr. Mengmeng Zhao , Dr. Wanfang Li

引用次数: 0

Abstract

We herein developed a mild and ligand‐free palladium‐catalyzed Heck‐Matsuda reaction between Morita‐Baylis‐Hillman alcohols (MBHAs) and aryl triazenes. After thorough screening of the acids, nitric acid (HNO₃) was unexpectedly found to be the most effective promoter for in situ generation of arenediazonium salts. This coupling reaction allows for a highly selective production of a various α‐arylmethyl β‐keto esters from readily accessible starting materials.

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钯催化Morita-Baylis-Hillman醇与芳基三氮烯的Heck-Matsuda反应：硝酸作为启动子的意外作用

本研究在Morita-Baylis-Hillman醇（MBHAs）和芳基三氮杂烯之间建立了一种温和的、无配体钯催化的Heck-Matsuda反应。经过对酸的彻底筛选，硝酸（HNO3）被意外地发现是原位生成arennediazonium盐的最有效的促进剂。这种偶联反应允许从容易获得的起始材料高度选择性地生产各种α -芳基甲基β -酮酯。

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来源期刊

European Journal of Organic Chemistry 化学-有机化学

CiteScore

5.40

自引率

3.60%

发文量

752

审稿时长

1 months

期刊介绍： The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.