Reactivity of 4-pyrimidyl Sulfonic Esters in Suzuki-Miyaura Cross-Coupling Reactions in Water Under Microwave Irradiation

被引：2

作者：

Vidal, Matias ^{[1
]}

Rodriguez-Aguilar, Jose ^{[1
]}

Aburto, Ignacio ^{[1
]}

Aliaga, Carolina ^{[1
,2
]}

Dominguez, Moises ^{[1
]}

机构：

[1] Univ Santiago Chile, Fac Quim & Biol, Av Bernardo OHiggins 3363, Santiago, Chile

[2] Univ Santiago Chile, Ctr Nanociencia & Nanotecnol CEDENNA, Av Bernardo OHiggins 3363, Santiago, Chile

来源：

CHEMISTRYSELECT | 2021年 / 6卷 / 45期

关键词：

Cross-coupling; Microwave; Pseudohalides; Pyrimidines; Suzuki-Miyaura reactions; PYRIMIDINES; ARYL; MOLECULE; LIGANDS; SYSTEMS; ACCESS; ACID; RING;

D O I：

10.1002/slct.202103280

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reactivity of four 4-pyrimidyl sulfonic esters in Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions was studied with various boronic acids. All the reactions were conducted in water under microwave irradiation. Electron-rich aryl boronic acids exhibited higher yields when triflate (-OSO2CF3) was used as the pseudohalide, whereas electron-poor aryl boronic acids reacted faster when nonaflate was employed (-OSO2(CF2)(3)CF3). Furthermore, the reactivity guide for Pd-catalyzed coupling of these accessible pseudohalides with boron-based coupling partners was applied to synthesize a bipyrimidine in excellent yield. Finally, the 2-methylpyrimidines obtained are suitable starting materials for the synthesis of luminescent sensors.

引用

页码：12858 / 12861

页数：4

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