Conditions for palladium-catalyzed direct arylations of 4-bromo and 4-iodo N-substituted pyrazoles without C-Br or C-I bond cleavage

被引：19
作者：
Brahim, Mariem [1 ,2 ]
Smari, Imen [1 ,2 ]
Ben Ammar, Hamed [2 ]
Ben Hassine, Bechir [2 ]
Soule, Jean-Francois [1 ]
Doucet, Henri [1 ]
机构：
[1] Univ Rennes 1, CNRS, UMR 6226, Inst Sci Chim Rennes,Organometall Mat & Catalyse, F-35042 Rennes, France
[2] Univ Monastir, Fac Sci Monastir, Lab Synth Organ Asymetr & Catalyse Homogene UR 11, Monastir 5000, Tunisia
来源：
ORGANIC CHEMISTRY FRONTIERS | 2015年 / 2卷 / 08期
关键词：
SUZUKI-MIYAURA REACTIONS; CROSS-COUPLING REACTIONS; HETEROAROMATIC-COMPOUNDS; RECENT PROGRESS; ARYL BROMIDES; H ARYLATION; FUNCTIONALIZATION; DERIVATIVES; DISCOVERY; HETEROARENES;
D O I：
10.1039/c5qo00093a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Pd-catalyzed arylation at the C5 position of N-protected pyrazole derivatives bearing bromo or iodo substituents at the C4 position is described. A simple phosphine-free catalytic system was used, namely, 1 mol% Pd(OAc)(2) in DMA in the presence of KOAc as the base. A wide aryl bromide scope as a coupling partner has been coupled with pyrazole derivatives. The reaction was very chemoselective as the C-halogen bonds of the pyrazole units were not involved in the C-H bond arylation process. Some examples demonstrating the synthetic potential of the bromo and iodo pyrazole substituents for chemical transformations are reported.
引用
收藏
页码：917 / 926
页数：10
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