Computational studies on CuAAC reaction mechanism with [CuX(PPh3)]; X = I, Br, Cl for the synthesis of 4-and 5-halo-1,2,3-triazoles

被引：9

作者：

Khairbek, Ali A. ^{[1
]}

Alzahrani, Abdullah Y. ^{[2
]}

Badawi, Mohammad Abd Al-Hakim ^{[1
]}

Thomas, Renjith ^{[3
,4
]}

机构：

[1] Tishreen Univ, Fac Sci, Dept Chem, Latakia, Syria

[2] King Khalid Univ, Fac Sci & Arts, Dept Chem, Mohail Assir, Saudi Arabia

[3] St Berchmans Coll Autonomous, Dept Chem, Changanassery 686101, Kerala, India

[4] St Berchmans Coll Autonomous, Ctr Theoret & Computat Chem, Changanassery 686101, Kerala, India

来源：

REACTION KINETICS MECHANISMS AND CATALYSIS | 2024年 / 137卷 / 02期

关键词：

Azide; Halo-triazoles; Copper; Cycloaddition; Click Chemistry; AZIDE-ALKYNE CYCLOADDITION; N-HETEROCYCLIC CARBENE; TERMINAL ALKYNES; ORGANIC AZIDES; COPPER; COMPLEXES; 1,2,3-TRIAZOLES; LIGATION; LIGANDS;

D O I：

10.1007/s11144-023-02548-z

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A complementary catalytic system was investigated for the [3 + 2] cycloaddition of azides and halo-alkynes. These are based on three copper complexes with [CuX (PPh3)]; X = I, Br, Cl, which are active at low metal loadings (the PPh3 system). The computational MN12-L approach showed acceptable results with levels of Def2-TZVPfor Cu and Def2-SVP for other elements. In general, all the computational results indicate that the cycloaddition reaction favors the formation of the observed 1,4-regioisomer (5-halo-triazoles) through a direct pi-activation mechanism.

引用

收藏

页码：777 / 790

页数：14

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