醇辅助的 C-C 键断裂：铜催化的β-酮酯和酰胺的去乙酰基α-芳基化反应。
Alcohol assisted C-C bond breaking: copper-catalyzed deacetylative α-arylation of β-keto esters and amides.
机构信息
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, Hubei, PR China.
出版信息
Chem Commun (Camb). 2013 Aug 4;49(60):6767-9. doi: 10.1039/c3cc43279c.
PMID:23778504
Abstract
A method of alcohol-assisted copper-catalyzed highly selective deacetylative α-arylation of β-keto esters and amides has been demonstrated, which illustrated an efficient example of achieving α-aryl esters and amides. From the synthetic point of view, this arylation protocol is general and practical, representing a simple way to produce α-arylated carbonyl compounds from basic starting materials at low cost.
摘要
已经证明了一种醇辅助的铜催化的β-酮酯和酰胺的高选择性去乙酰基α-芳基化方法，该方法为实现α-芳基酯和酰胺提供了一个有效的例子。从合成的角度来看，该芳基化方案具有普遍性和实用性，代表了一种从基本原料低成本合成α-芳基羰基化合物的简单方法。
相似文献
1
Alcohol assisted C-C bond breaking: copper-catalyzed deacetylative α-arylation of β-keto esters and amides.
Chem Commun (Camb). 2013 Aug 4;49(60):6767-9. doi: 10.1039/c3cc43279c.
2
Facile access to polysubstituted indoles via a cascade Cu-catalyzed arylation-condensation process.
J Org Chem. 2007 Nov 23;72(24):9329-34. doi: 10.1021/jo702059q. Epub 2007 Nov 2.
3
Copper-TBAF catalyzed arylation of amines and amides with aryl trimethoxysilane.
Org Biomol Chem. 2009 Mar 7;7(5):869-73. doi: 10.1039/b819510b. Epub 2009 Jan 20.
4
A beta-keto ester as a novel, efficient, and versatile ligand for copper(I)-catalyzed C-N, C-O, and C-S coupling reactions.
J Org Chem. 2007 May 11;72(10):3863-7. doi: 10.1021/jo070443m. Epub 2007 Apr 14.
5
Enantioselective and Regiodivergent Copper-Catalyzed Electrophilic Arylation of Allylic Amides with Diaryliodonium Salts.
J Am Chem Soc. 2015 Jul 1;137(25):7986-9. doi: 10.1021/jacs.5b03937. Epub 2015 Jun 19.
6
Room-temperature copper-catalyzed alpha-arylation of malonates.
Org Lett. 2007 Aug 16;9(17):3469-72. doi: 10.1021/ol701473p. Epub 2007 Jul 18.
7
Palladium-catalyzed arylation of trimethylsilyl enolates of esters and imides. High functional group tolerance and stereoselective synthesis of alpha-aryl carboxylic acid derivatives.
J Am Chem Soc. 2004 Apr 28;126(16):5182-91. doi: 10.1021/ja031544e.
8
DNA-catalyzed hydrolysis of esters and aromatic amides.
J Am Chem Soc. 2013 Oct 30;135(43):16014-7. doi: 10.1021/ja4077233. Epub 2013 Oct 17.
9
Copper-catalyzed one-pot trifluoromethylation/aryl migration/desulfonylation and C(sp2)-N bond formation of conjugated tosyl amides.
J Am Chem Soc. 2013 Oct 2;135(39):14480-3. doi: 10.1021/ja403954g. Epub 2013 Sep 18.
10
NHC-catalyzed C-O or C-N bond formation: efficient approaches to α,β-unsaturated esters and amides.
Chem Commun (Camb). 2012 Jul 25;48(58):7280-2. doi: 10.1039/c2cc32862c. Epub 2012 Jun 14.
Zotero 插件