A Modular Sydnone Cycloaddition/Suzuki-Miyaura Cross-Coupling Strategy to Unsymmetrical 3,5-Bis(hetero)aromatic Pyrazoles

被引：58

作者：

Delaunay, Thierry ^{[1
]}

Genix, Pierre ^{[2
]}

Es-Sayed, Mazen ^{[2
]}

Vors, Jean-Pierre ^{[2
]}

Monteiro, Nuno ^{[1
]}

Balme, Genevieve ^{[1
]}

机构：

[1] Univ Lyon 1, ESCPE Lyon, CNRS, UMR 5246,ICBMS,Inst Chim & Biochim Mol & Supramol, F-69622 Villeurbanne, France

[2] Bayer CropSci, Bayer SAS, F-69263 Lyon 09, France

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 15期

关键词：

ONE-POT SYNTHESIS; REGIOSELECTIVE SYNTHESIS; HALOGENATED NITROGEN; FUNCTIONALIZATION; CHEMISTRY; ARYLATION; ORIGIN; ACCESS; OXYGEN; ROUTE;

D O I：

10.1021/ol101087j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The [3 + 2] dipolar cycloaddition of 4-halosydnones with 1-haloalkynes opens a straightforward access to 3,5-dihalopyrazoles, valuable scaffolds for the elaboration of unsymmetrically 3,5-substituted pyrazole derivatives via site-selective Pd-catalyzed cross-coupling reactions. For instance, the flexible introduction of different (hetero)aryl substituents at the C-5 and C-3 positions of the PMP-protected pyrazole nucleus was achieved in a one-pot operation via sequential reactions with various boronic acids.

引用

页码：3328 / 3331

页数：4

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