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烯醇盐介导的有机催化叠氮化物-酮[3+2]环加成反应:全官能化1,2,3-三唑的区域选择性高产率合成

An enolate-mediated organocatalytic azide-ketone [3+2]-cycloaddition reaction: regioselective high-yielding synthesis of fully decorated 1,2,3-triazoles.

作者信息

Shashank Adluri B, Karthik S, Madhavachary R, Ramachary Dhevalapally B

机构信息

Catalysis Laboratory, School of Chemistry, University of Hyderabad, Hyderabad-500 046 (India), Fax: (+91) 40-23012460.

出版信息

Chemistry. 2014 Dec 15;20(51):16877-81. doi: 10.1002/chem.201405501. Epub 2014 Nov 3.

Abstract

An enolate-mediated organocatalytic azide-ketone [3+2]-cycloaddition (OrgAKC) reaction of a variety of enolizable arylacetones and deoxybenzoins with aryl azides was developed for the synthesis of fully decorated 1,4-diaryl-5-methyl(alkyl)-1,2,3-triazoles in excellent yields with high regioselectivity at 25 °C for 0.5-6 h. This reaction has an excellent outcome with reference to reaction rate, yield, regioselectivity, operation simplicity, and availability of substrates and catalyst. This reaction has advantages over the previously known metal-mediated reactions.

摘要

开发了一种烯醇盐介导的有机催化叠氮化物-酮[3+2]环加成(OrgAKC)反应,用于各种可烯醇化的芳基丙酮和脱氧苯偶姻与芳基叠氮化物反应,以优异的产率和高区域选择性在25°C下反应0.5-6小时,合成完全修饰的1,4-二芳基-5-甲基(烷基)-1,2,3-三唑。该反应在反应速率、产率、区域选择性、操作简便性以及底物和催化剂的可得性方面都有出色的结果。与先前已知的金属介导反应相比,该反应具有优势。

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