Carbene insertion to N-H bonds of 2-aminothiazole and 2-amino-1,3,4-thiadiazole derivatives catalyzed by iron phthalocyanine

被引：5

作者：

Cailler, Lucie P. ^{[1
]}

Martynov, Alexander G. ^{[2
]}

Gorbunova, Yulia G. ^{[2
]}

Tsivadze, Asian Yu ^{[2
]}

Sorokin, Alexander B. ^{[1
]}

机构：

[1] Univ Lyon 1, Inst Rech Catalyse & Environm Lyon, IRCELYON, UMR 5256,CNRS, 2 Av Albert Einstein, F-69626 Villeurbanne, France

[2] Russian Acad Sci, AN Frumkin Inst Phys Chem & Electrochem, Leninskii Pr 31,Bldg 4, Moscow 119071, Russia

来源：

JOURNAL OF PORPHYRINS AND PHTHALOCYANINES | 2019年 / 23卷 / 4-5期

关键词：

catalysis; phthalocyanine; carbene transfer; amines; thiazole; thiadiazole; thiazoline; ethyl diazoacetate; CHLORINATED PHENOLS; OPTICAL-PROPERTIES; SYNTHETIC USES; PORPHYRIN; OXIDATION; CYCLOPROPANATION; REACTIVITY; COMPLEXES; WATER; DFT;

D O I：

10.1142/S1088424619500354

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Iron(III) phthalocyaninate decorated with crown ether substituents, [(15C5)(4)PcFe]Cl, efficiently catalyzed the insertion of carbene derived from ethyl diazoacetate to six amines functionalized with thiazole, thiazoline and thiadiazole heterocycles. The reactions were carried out under practical conditions using EDA:amine stoechiometric ratio with 0.05 mol% catalyst loading. Turnover numbers up to 3360 have been achieved. The aminoacid derivatives bearing heterocyclic moieties were obtained under catalytic conditions for the first time with 36-69% yields in the case of single N-H insertion products and up to 77% in the case of double N-H insertion products.

引用

页码：497 / 506

页数：10

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