Ruthenium-Catalyzed CH Bond Activation of Michael Acceptors: An Unusual Reactivity Leading to Allylsilanes

✍ Scribed by Marc-Olivier Simon; Rémi Martinez; Jean-Pierre Genêt; Sylvain Darses

• Publisher: John Wiley and Sons
• Year: 2009
• Tongue: English
• Weight: 181 KB
• Volume: 351
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/adsc.200800600

✦ Synopsis

Abstract

We report here an improved catalyst for the functionalization of Michael acceptors, involving CC bond formation via CH bond activation, using an in situ generated ruthenium active species. Moreover, on some particular substrates, the CH functionalization resulted unexpectedly in the formation of allylsilanes rather than in the expected conjugated adducts, affording a new straightforward methodology to access useful stereodefined trisubstituted allylsilanes via CH bond activation. Preliminary results have shown that they were reactive in the allylation of aldehydes, providing an access to alcohols bearing a quaternary carbon center.