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铜(Ⅰ)试剂促进的烯酰胺羟基三氟甲基化反应:取代-3-羟基-2-芳基-3-(2,2,2-三氟-1-芳基乙基)异吲哚啉-1-酮的灵活合成

Copper(i) reagent-promoted hydroxytrifluoromethylation of enamides: flexible synthesis of substituted-3-hydroxy-2-aryl-3-(2,2,2-trifluoro-1-arylethyl)isoindolin-1-one.

作者信息

Wang Qing, Shi Peng, Zeng Runsheng

机构信息

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry Chemical Engineering and Materials Science, Soochow University Suzhou Jiangsu 215123 China

出版信息

RSC Adv. 2018 Jul 19;8(46):25961-25965. doi: 10.1039/c8ra04088e.

DOI:10.1039/c8ra04088e
PMID:35541984
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9082868/
Abstract

A novel CuBr-catalyzed hydroxytrifluoromethylation reaction was investigated. Substituted 3-benzylidene-2-arylisoindolin-1-ones was reacted with sodium trifluoromethanesulfinate to afford substituted-3-hydroxy-2-aryl-3-(2,2,2-trifluoro-1-arylethyl)isoindolin-1-one. The reaction proceeded at 25 °C in air atmosphere in the absence of base and ligands. Our results indicate that trifluoromethyl free radical tends to attack a double bond rather than aryl in this reaction.

摘要

研究了一种新型的溴化铜催化的羟基三氟甲基化反应。将取代的3-亚苄基-2-芳基异吲哚啉-1-酮与三氟甲亚磺酸钠反应,得到取代的3-羟基-2-芳基-3-(2,2,2-三氟-1-芳基乙基)异吲哚啉-1-酮。该反应在25℃、空气氛围、无碱和配体的条件下进行。我们的结果表明,在该反应中三氟甲基自由基倾向于进攻双键而非芳基。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1d7c/9082868/3b6f048e67d4/c8ra04088e-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1d7c/9082868/ba667872868c/c8ra04088e-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1d7c/9082868/80a7b91fe4be/c8ra04088e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1d7c/9082868/0a667d172861/c8ra04088e-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1d7c/9082868/3b6f048e67d4/c8ra04088e-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1d7c/9082868/ba667872868c/c8ra04088e-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1d7c/9082868/80a7b91fe4be/c8ra04088e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1d7c/9082868/0a667d172861/c8ra04088e-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1d7c/9082868/3b6f048e67d4/c8ra04088e-s3.jpg

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