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铜催化酰胺的 N-芳基化反应,使用 (S)-N-甲基吡咯烷-2-羧酸酯作为配体。

Copper-catalyzed N-arylation of amides using (S)-N-methylpyrrolidine-2-carboxylate as the ligand.

机构信息

College of Chemical Engineering and Material, Heilongjiang University, Haerbin 150080, China.

出版信息

Molecules. 2010 Mar 2;15(3):1154-60. doi: 10.3390/molecules15031154.

DOI:10.3390/molecules15031154
PMID:20335970
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6257265/
Abstract

(S)-N-methylpyrrolidine-2-carboxylate, a derivative of natural L-proline, was found to be an efficient ligand for the copper-catalyzed Goldberg-type N-arylation of amides with aryl halides under mild conditions. A variety of N-arylamides were synthesized in good to high yields.

摘要

(S)-N-甲基吡咯烷-2-羧酸,一种天然 L-脯氨酸的衍生物,被发现是一种有效的配体,可在温和条件下促进铜催化的酰胺与芳基卤化物的 Goldberg 型 N-芳基化反应。多种 N-芳酰胺以良好到高产率合成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fefe/6257265/5ccccecc8a4b/molecules-15-01154-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fefe/6257265/5ccccecc8a4b/molecules-15-01154-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fefe/6257265/5ccccecc8a4b/molecules-15-01154-g001.jpg

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本文引用的文献

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J Org Chem. 2007 Oct 26;72(22):8535-8. doi: 10.1021/jo0712289. Epub 2007 Sep 29.
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Copper-catalyzed N-arylation of imidazoles and benzimidazoles.铜催化的咪唑和苯并咪唑的N-芳基化反应。
J Org Chem. 2007 Aug 3;72(16):6190-9. doi: 10.1021/jo070807a. Epub 2007 Jul 11.
3
A beta-keto ester as a novel, efficient, and versatile ligand for copper(I)-catalyzed C-N, C-O, and C-S coupling reactions.
一种β-酮酯作为用于铜(I)催化的C-N、C-O和C-S偶联反应的新型、高效且通用的配体。
J Org Chem. 2007 May 11;72(10):3863-7. doi: 10.1021/jo070443m. Epub 2007 Apr 14.
4
Efficient iron/copper co-catalyzed arylation of nitrogen nucleophiles.铁/铜高效共催化氮亲核试剂的芳基化反应
Angew Chem Int Ed Engl. 2007;46(6):934-6. doi: 10.1002/anie.200603173.
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1,1,1-tris(hydroxymethyl)ethane as a new, efficient, and versatile tripod ligand for copper-catalyzed cross-coupling reactions of aryl iodides with amides, thiols, and phenols.1,1,1-三(羟甲基)乙烷作为一种新型、高效且通用的三脚架配体,用于铜催化芳基碘化物与酰胺、硫醇和酚的交叉偶联反应。
Org Lett. 2006 Nov 23;8(24):5609-12. doi: 10.1021/ol062339h.
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Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles.氨基酸促进了碘化亚铜催化的芳基卤化物与胺或含氮杂环之间的碳氮键形成。
J Org Chem. 2005 Jun 24;70(13):5164-73. doi: 10.1021/jo0504464.
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