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Synfacts 2015; 11(1): 0075
DOI: 10.1055/s-0034-1379660
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Cross-Coupling of Triorganoindium Reagents

Contributor(s):
Paul Knochel
,
Jeffrey M. Hammann
Pérez-Caaveiro C, Sestelo JP, Martínez MM, * Sarandeses LA. * Universidade de Coruña, Spain
Triorganoindium Reagents in Selective Palladium-Catalyzed Cross-Coupling with Iodoimidazoles: Synthesis of Neurodazine.

J. Org. Chem. 2014;
79: 9586-9593
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Further Information

Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

indium - palladium - imidazoles

Significance

The authors demonstrate that tri­organoindium reagents react selectively with N-benzyl-2,4,5-triiodoimidazole under palladium ­catalysis to give the corresponding C-2-arylated coupling products in good yields. These products can further be used in a subsequent double cross-coupling to afford trisubstituted imidazoles in good yields.


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Comment

This methodology was further applied to the synthesis of neurodazine, a biologically active compound which is able to specifically induce neurogenesis of non-pluripotent myoblasts and the cells derived from mature human skeletal muscle.


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