Au(I)-Catalyzed Regioselective Hydrogen Isotope Labeling of Indoles.

Autor:	Milcendeau P; Université Paris-Saclay, CNRS, Institut de Chimie des Substances Naturelles, UPR 2301, 91198 Gif-sur-Yvette, France., Colonna P; Université Paris-Saclay, Département Médicaments et Technologies pour la Santé, SCBM, CEA, INRAE, 91191 Gif-sur-Yvette, France., Ramdani M; Université Paris-Saclay, CNRS, Institut de Chimie des Substances Naturelles, UPR 2301, 91198 Gif-sur-Yvette, France., Garcia-Argote S; Université Paris-Saclay, Département Médicaments et Technologies pour la Santé, SCBM, CEA, INRAE, 91191 Gif-sur-Yvette, France., Glinsky-Olivier N; Université Paris-Saclay, CNRS, Institut de Chimie des Substances Naturelles, UPR 2301, 91198 Gif-sur-Yvette, France., Pieters G; Université Paris-Saclay, Département Médicaments et Technologies pour la Santé, SCBM, CEA, INRAE, 91191 Gif-sur-Yvette, France., Guinchard X; Université Paris-Saclay, CNRS, Institut de Chimie des Substances Naturelles, UPR 2301, 91198 Gif-sur-Yvette, France.
Jazyk:	angličtina
Zdroj:	Organic letters [Org Lett] 2024 Nov 15; Vol. 26 (45), pp. 9735-9740. Date of Electronic Publication: 2024 Nov 05.
DOI:	10.1021/acs.orglett.4c03597
Abstrakt:	The gold(I)-catalyzed hydrogen isotope exchange reaction on indoles and related heterocycles is described under mild conditions and low catalyst loadings, using CD 3 OD and D 2 O 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.
Databáze:	MEDLINE
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