Enantiospecific CH Activation Using Ruthenium Nanocatalysts

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 s...

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Veröffentlicht in:Angewandte Chemie International Edition 2015-09, Vol.54 (36), p.10474-10477
Hauptverfasser: Taglang, Céline, Martínez-Prieto, Luis Miguel, del Rosal, Iker, Maron, Laurent, Poteau, Romuald, Philippot, Karine, Chaudret, Bruno, Perato, Serge, Sam Lone, Anaïs, Puente, Céline, Dugave, Christophe, Rousseau, Bernard, Pieters, Grégory
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Sprache:eng
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Zusammenfassung: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. Various compounds, such as amines, amino acids, or peptides, can undergo enantiospecific CH activation/deuteration in the presence of ruthenium nanocatalysts under mild conditions. Theoretical studies revealed a four‐membered dimetallacycle as the key intermediate and suggested that the collective motion of surface species can facilitate the CH activation step by modulating the local electronic structure.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201504554