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铁催化硫酯与有机锰试剂的交叉偶联反应。

Iron-Catalyzed Cross-Coupling of Thioesters and Organomanganese Reagents.

机构信息

Institute of Organic Chemistry, Faculty of Science, Eberhard Karls University Tübingen, Auf der Morgenstelle 18, 72076, Tübingen, Germany.

i-CLeHS, UMR 8060, CNRS Chimie ParisTech, 11, rue Pierre et Marie Curie, 75005, Paris, France.

出版信息

Chemistry. 2022 Nov 7;28(62):e202202212. doi: 10.1002/chem.202202212. Epub 2022 Sep 1.

DOI:10.1002/chem.202202212
PMID:35869871
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9804419/
Abstract

We report a Fukuyama-type coupling of thioesters with aliphatic organomanganese reagents utilizing a cheap and easily available iron(III) precatalyst. The reactions exhibit a wide tolerance of solvents and functional groups, allowing for the conversion of thioesters derived from natural products and pharmaceutical compounds. A strong steric impact from each reaction component (carboxylic moiety, thiol substituent and manganese reagent) was displayed, which enabled regioselective transformation of dithioesters. Mechanistic investigations showed that the released thiolate does not act as a mere spectator ligand, but rather positively influences the stability of intermediate alkyl(II)ferrates.

摘要

我们报告了一种利用廉价易得的铁(III)前催化剂实现硫酯与脂肪族有机锰试剂的福山型偶联。该反应对溶剂和官能团具有广泛的耐受性，允许将天然产物和药物化合物衍生的硫酯进行转化。每个反应组分（羧酸部分、硫醇取代基和锰试剂）都表现出强烈的空间位阻，从而能够实现二硫酯的区域选择性转化。机理研究表明，释放出的硫醇盐不是仅仅作为一个旁观配体，而是积极影响中间烷基(II)铁酸盐的稳定性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5984/9804419/013440ad0b96/CHEM-28-0-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5984/9804419/74c5c2e332df/CHEM-28-0-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5984/9804419/69af6a407cb3/CHEM-28-0-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5984/9804419/65e0f4006650/CHEM-28-0-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5984/9804419/907129826780/CHEM-28-0-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5984/9804419/639d22abce5e/CHEM-28-0-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5984/9804419/790d373f1bf7/CHEM-28-0-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5984/9804419/1289fd560727/CHEM-28-0-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5984/9804419/117691460fb6/CHEM-28-0-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5984/9804419/d929be6c0f79/CHEM-28-0-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5984/9804419/013440ad0b96/CHEM-28-0-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5984/9804419/74c5c2e332df/CHEM-28-0-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5984/9804419/69af6a407cb3/CHEM-28-0-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5984/9804419/65e0f4006650/CHEM-28-0-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5984/9804419/907129826780/CHEM-28-0-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5984/9804419/639d22abce5e/CHEM-28-0-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5984/9804419/790d373f1bf7/CHEM-28-0-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5984/9804419/1289fd560727/CHEM-28-0-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5984/9804419/117691460fb6/CHEM-28-0-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5984/9804419/d929be6c0f79/CHEM-28-0-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5984/9804419/013440ad0b96/CHEM-28-0-g009.jpg

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