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Angew Chem Int Ed Engl. 2015 Sep 01;54(36):10474-7. doi: 10.1002/anie.201504554.

Enantiospecific C-H Activation Using Ruthenium Nanocatalysts.

Angewandte Chemie (International ed. in English)

Céline Taglang, Luis Miguel Martínez-Prieto, Iker del Rosal, Laurent Maron, Romuald Poteau, Karine Philippot, Bruno Chaudret, Serge Perato, Anaïs Sam Lone, Céline Puente, Christophe Dugave, Bernard Rousseau, Grégory Pieters

Affiliations

  1. CEA Saclay, SCBM, iBiTec-S, Building 547, PC # 108, 91191 Gif sur Yvette (France).
  2. 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).
  3. CNRS; LCC (Laboratoire de Chimie de Coordination), 205, Route de Narbonne, 31077 Toulouse (France).
  4. CEA Saclay, SCBM, iBiTec-S, Building 547, PC # 108, 91191 Gif sur Yvette (France). [email protected].

PMID: 26371960 DOI: 10.1002/anie.201504554

Abstract

The activation of C-H bonds has revolutionized modern synthetic chemistry. However, no general strategy for enantiospecific C-H activation has been developed to date. We herein report an enantiospecific C-H activation reaction followed by deuterium incorporation at stereogenic centers. Mechanistic studies suggest that the selectivity for the α-position of the directing heteroatom results from a four-membered dimetallacycle as the key intermediate. This work paves the way to novel molecular chemistry on nanoparticles.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: CH activation; ab initio calculations; deuterium; isotopic labeling; nanoparticles

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