One-pot catalytic C–C double bond cleavage of α,β-enones aided by alkyl group-immobilized silica spheres

✍ Scribed by Dong Hun Lee; Eun-Ae Jo; Jung-Woo Park; Chul-Ho Jun

• Book ID: 104097111
• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 448 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2009.10.103

✦ Synopsis

Catalytic C-C double bond cleavage of a,b-enones with a 1-alkene and H 2 O was carried out in the presence of a (Ph 3 P) 3 RhCl catalyst, 2-amino-3-picoline, cyclohexylamine, benzoic acid, and alkyl groupimmobilized silica spheres. Upon completion of the reaction, the corresponding ketones were obtained without needing a further hydrolysis step. In this reaction, alkyl group-immobilized silica spheres act as a water reservoir for hydrolysis of an intermediate ketimine and as a phase divider between the organic solution and H 2 O.