Rhodium-catalyzed conjugate addition of arylindium reagents to α,β-unsaturated carbonyl compounds.

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


Tetrahedron 2012, 68, 1606–1611 (DOI: 10.1016/j.tet.2011.11.075).

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A novel rhodium-catalyzed conjugate addition of indium reagents to electron deficient olefins is reported. The reaction takes place in THF/MeOH at 110 °C using arylindium dichlorides, a rhodium(I)-binap complex as catalyst, and α,β-unsaturated ketones and lactones in good yields (45–94%). The addition of MeOH is crucial for an efficient transformation and NMR studies seem to indicate that promotes the catalytic cycle leaving the indium organometallic unaltered. The use of chiral non-racemic ligands allows performing the reaction with moderate enantioselectivities.