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  • Title: A modular sydnone cycloaddition/Suzuki-Miyaura cross-coupling strategy to unsymmetrical 3,5-bis(hetero)aromatic pyrazoles.
    Author: Delaunay T, Genix P, Es-Sayed M, Vors JP, Monteiro N, Balme G.
    Journal: Org Lett; 2010 Aug 06; 12(15):3328-31. PubMed ID: 20597542.
    Abstract:
    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.
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