Rhodium-catalyzed allylic substitution reactions using indium(III) organometallics.

Riveiros, R.; Tato, R.; Pérez Sestelo, J.; Sarandeses, L. A.


Eur. J. Org. Chem. 2012, 3018–3023 (DOI: 10.1002/ejoc.201200104).

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A novel rhodium-catalyzed allylic substitution reaction using indium organometallics is reported. Aryl- and heteroarylindium reagents reacted in THF at 80 °C with primary and secondary allyl halides and their derivatives under rhodium(I) catalysis to afford the α-substituted products in good yields and with high regio- and stereoselectivity. The reaction takes place with substoichiometric amounts of the triorganoindium reagents, which demonstrates the efficiency of the indium–rhodium transmetallation process in carbon–carbon bond-forming reactions.