Phosphine catalyzed alpha-arylation of enones and enals using hypervalent bismuth reagents: regiospecific enolate arylation via nucleophilic catalysis.
Exposure of enones and enals to 20 mol % tributylphosphine in the presence of triarylbismuth(V) dichlorides results in regiospecific aryl transfer to the alpha-position of the enone or enal pronucleophile. These results represent the first examples of enolate arylation under the conditions of nucleophilic catalysis.
Koech
Phillip K
PK
Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712, USA.
Krische
Michael J
MJ
D000447:Aldehydes / Q000737:chemistry*; D001729:Bismuth / Q000737:chemistry*; D002384:Catalysis; D003512:Cyclohexanones / Q000737:chemistry*; D003517:Cyclopentanes / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry; D015394:Molecular Structure; D010720:Phosphines / Q000737:chemistry*
D000447:Aldehydes; D003512:Cyclohexanones; D003517:Cyclopentanes; D007202:Indicators and Reagents; D010720:Phosphines; C012796:2-butenal; C044646:phosphine; C013905:cyclopentenone; D001729:Bismuth