Triorganoindium Reagents in Selective Palladium-Catalyzed Cross-Coupling With Iodoimidazoles: Synthesis of Neurodazine

Cristina Pérez-Caaveiro, José Pérez Sestelo, M Montserrat Martínez, Luis A Sarandeses

J Org Chem. 2014 Oct 17;79(20):9586-93.

PMID: 25203769

Abstract:

Triorganoindium reagents (R3In, R = aryl, heteroaryl, alkynyl) react selectively under palladium catalysis with N-benzyl-2,4,5-triiodoimidazole to afford the C-2 monocoupling products. The reaction proceeds efficiently for a variety of aryl- and heteroarylindium reagents with the transfer of all three organic groups attached to the metal. The coupling products can be used in a subsequent two-fold cross-coupling to give trisubstituted imidazoles in good yields. This approach was employed to synthesize neurodazine and analogues in good yields.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP937807664-A	Neurodazine		937807-66-4	Price