Au(I)-catalyzed Regioselective Hydrogen Isotope Labeling of Indoles 6f, 8 - Archive ouverte HAL
Article Dans Une Revue Organic Letters Année : 2024

Au(I)-catalyzed Regioselective Hydrogen Isotope Labeling of Indoles 6f, 8

Résumé

The gold(I)-catalyzed hydrogen isotope exchange reaction on indoles and related heterocycles is described under mild conditions and low catalyst loadings, using CD3OD and D2O as readily available deuterium sources. C3-unsubstituted indoles are labeled at the C3 position with exquisite regioselectivity, while C3-substituted indoles are labeled at the C2 position. The method is also applicable to the regioselective tritiation of indoles. Mechanistic studies revealed the involvement of aurated indoles as key intermediates
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Dates et versions

hal-04788467 , version 1 (18-11-2024)

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Pierre Milcendeau, Pierre Colonna, Mohammed Ramdani, Sébastien Garcia-Argote, Nicolas Glinsky-Olivier, et al.. Au(I)-catalyzed Regioselective Hydrogen Isotope Labeling of Indoles 6f, 8. Organic Letters, 2024, 26 (45), pp.9735-9740. ⟨10.1021/acs.orglett.4c03597⟩. ⟨hal-04788467⟩
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