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在有氧条件下,通过钯碘催化的氧化环化-脱保护-烷氧基羰化序列合成苯并噻吩-3-羧酸酯。

Synthesis of Benzothiophene-3-carboxylic Esters by Palladium Iodide-Catalyzed Oxidative Cyclization-Deprotection-Alkoxycarbonylation Sequence under Aerobic Conditions.

机构信息

Laboratory of Industrial and Synthetic Organic Chemistry (LISOC), Department of Chemistry and Chemical Technologies, University of Calabria, Via Pietro Bucci 12/C, 87036 Arcavacata di Rende (CS), Italy.

出版信息

J Org Chem. 2023 Apr 21;88(8):5180-5186. doi: 10.1021/acs.joc.2c00686. Epub 2022 May 10.

DOI:10.1021/acs.joc.2c00686
PMID:35537181
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10127270/
Abstract

A palladium-catalyzed carbonylative approach to benzothiophene-3-carboxylic esters, starting from simple and readily available building blocks [2-(methylthio)phenylacetylenes, CO, an alcohol, and O (from air)], is reported. The process is catalyzed by the simple PdI/KI catalytic system to give the desired products in fair to high yields (57-83%). Interestingly, the reaction also works nicely in the ionic liquid BmimBF as the solvent, with the possibility to recycle the catalytic system several times without appreciable loss of activity.

摘要

报道了一种钯催化的羰基化方法,用于从简单易得的起始原料[2-(甲硫基)苯乙炔、CO、醇和 O(来自空气)]合成苯并噻吩-3-羧酸酯。该过程由简单的 PdI/KI 催化体系催化,以中等至较高的收率(57-83%)得到所需产物。有趣的是,该反应在离子液体 BmimBF 中也能很好地进行,并且有可能多次回收催化体系而活性没有明显损失。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eb0f/10127270/0d587a99adf7/jo2c00686_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eb0f/10127270/0d587a99adf7/jo2c00686_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eb0f/10127270/0d587a99adf7/jo2c00686_0001.jpg

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