通过 Rh(II)-Catalyzed N-H Insertion（涉及结构多样的重氮试剂）对 NH-四唑进行简便 N-修饰

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry Pub Date : 2024-11-20 DOI:10.1002/ejoc.202401138

Valentin Radiupov, Grigory Kantin, Dmitry Dar'in

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引用次数: 0

摘要

通过 Rh(II) 催化的重氮羰基化合物插入 N-H 键的反应，提出了一种对 NH-四唑进行 N-修饰的简便方法。多种结构不同的重氮试剂（包括杂环试剂）以及在第五位具有不同取代基的四唑都可以用来制备 2,5-二取代的四唑衍生物，而且产量高，具有很高的区域选择性。研究表明，当四氮唑中存在取电子基团以及质子酸时，反应的区域选择性会降低。

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Facile N-Modification of NH-Tetrazoles via Rh(II)-Catalyzed N-H Insertion Involving Structurally Diverse Diazo Reagents

A convenient method for the N-modification of NH-tetrazoles by the Rh(II)-catalyzed insertion reaction of diazocarbonyl compounds into the N-H bond has been proposed. A wide range of structurally diverse diazo reagents (including heterocyclic ones) as well as tetrazoles with different substituents in the fifth position can be used to prepare 2,5-disubstituted tetrazole derivatives in good and high yields and with high regioselectivity. It is shown that the regioselectivity of the reaction can decrease in the presence of electron withdrawing groups in the tetrazole, as well as in the presence of proton acids.

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来源期刊

European Journal of Organic Chemistry 化学-有机化学

CiteScore

5.40

自引率

3.60%

发文量

752

审稿时长

1 months

期刊介绍： The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.