Triorganoindium reagents in selective palladium catalyzed cross-coupling with iodoimidazoles: synthesis of neurodazine.

Pérez-Caaveiro, C.; Pérez Sestelo, J.; Martínez, M. M.; Sarandeses, L. A.


J. Org. Chem. 2014, 79, 9586–9593 (DOI: 10.1021/jo501664p).
Highlighted in: Knochel, P.; Hammann, J. M. Synfacts 2015, 11, 75 (DOI: 10.1055/s-0034-1379660).

trigger text
hidden content

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.