Ruthenium-catalyzed hydrogen isotope exchange of C(sp3)–H bonds directed by a sulfur atom

Longhui Gao; Serge Perato; Sébastien Garcia-Argote; Céline Taglang; Luis Miguel Martínez-Prieto; Céline Chollet; David-Alexandre Buisson; Vincent Dauvois; Philippe Lesot; Bruno Chaudret; Bernard Rousseau; Sophie Feuillastre; Grégory Pieters

doi:10.1039/C8CC00653A

Ruthenium-catalyzed hydrogen isotope exchange of C(sp³)–H bonds directed by a sulfur atom†

Longhui Gao,^a Serge Perato,^a Sébastien Garcia-Argote,^a Céline Taglang,^a Luis Miguel Martínez-Prieto,

^b Céline Chollet,^a David-Alexandre Buisson,^a Vincent Dauvois,^c Philippe Lesot,^d Bruno Chaudret,

^b Bernard Rousseau,^a Sophie Feuillastre^a and Grégory Pieters*^a

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* Corresponding authors

^a SCBM, CEA, Université Paris Saclay, Gif-sur-Yvette, France
E-mail: gregory.pieters@cea.fr

^b LPCNO, Laboratoire de Physique et Chimie de Nano-Objets, UMR 5215 INSA-CNRS-UPS, Institut National des Sciences Appliquées, 135, Avenue de Rangueil, 31077 Toulouse, France

^c CEA Saclay, DEN/DANS/DPC/SECR/LRMO, 91191 Gif sur Yvette, France

^d RMN en Milieu Orienté, ICMMO, UMR CNRS 8182, Université Paris-Sud/Université Paris-Saclay, Bât. 410, 91405 Orsay cedex, France

Abstract

We present here the first example of C(sp³)–H activation directed by a sulfur atom. Based on this transformation catalyzed by Ru/C, we have developed a hydrogen isotope exchange reaction for the deuterium and tritium labelling of thioether substructures in complex molecules.

Chemical Communications

Ruthenium-catalyzed hydrogen isotope exchange of C(sp³)–H bonds directed by a sulfur atom†

Abstract

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