N²-Alkylation of 1,2,3-Triazoles with Ethers under Thermodynamical Control.

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-02-14 Epub Date: 2025-01-31 DOI:10.1021/acs.orglett.4c04754

Hui Zhang, Zijian Zhang, Lifang Tian, Yanfeng Han, Peijun Zhao, Honglei Yang, Jiawei Li, Guanglu Liu, Li-Li Zhu, Yahui Wang

引用次数: 0

Abstract

Herein, a relay strategy incorporating oxidative cross dehydrogenative coupling (CDC) and N¹- to N²-isomerization is disclosed for the formal N²-selective alkylation of triazoles with ethers under thermodynamic control conditions. By taking advantage of the different thermodynamical stabilities of N¹- and N²-alkylated triazoles (3.65 kcal/mol), the initially formed N¹-isomers can be in situ converted into their more stable N²-isomers when reaching thermodynamic equilibrium. PhI(OAc)₂ has been discovered to function as both an oxidant for the CDC process and an efficient mediator for the isomerization step.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.

N2-Alkylation of 1,2,3-Triazoles with Ethers under Thermodynamical Control.

Abstract

N²-Alkylation of 1,2,3-Triazoles with Ethers under Thermodynamical Control.