Simple alkenes as substitutes for organometallic reagents: nickel-catalyzed, intermolecular coupling of aldehydes, silyl triflates, and alpha olefins.
A nickel-catalyzed method for the three-component coupling of alkenes (ethylene and alpha olefins), aldehydes, and silyl triflates is described, and this process represents the first catalytic method for coupling aldehydes and alkenes to give allylic alcohol derivatives. Conceptually, the alkene functions as a replacement for an alkenylmetal reagent.
Ng
Sze-Sze
SS
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA.
Jamison
Timothy F
TF
D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D017646:Organosilicon Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D000475:Alkenes; D009942:Organometallic Compounds; D017646:Organosilicon Compounds; D009532:Nickel