Multicatalytic synthesis of alpha-pyrrolidinyl ketones via a tandem palladium(II)/indium(III)-catalyzed aminochlorocarbonylation/Friedel-Crafts acylation reaction.
An oxidative carbonylation reaction that generates acid chloride functionality has been developed. Furthermore, this aminochlorocarbonylation reaction has been merged with a catalytic Friedel-Crafts acylation to produce a highly efficient tandem multicatalytic synthesis of pyrrolidinyl ketones. Significant variation of the aromatic nucleophile and substrate are shown. Two examples of incorporation of this method in triple-catalytic sequences are also demonstrated.
Cernak
Tim A
TA
Department of Chemistry, Columbia University, New York, New York 10027, USA.
Lambert
Tristan H
TH
D000215:Acylation; D002384:Catalysis; D007204:Indium / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism
D007659:Ketones; D011759:Pyrrolidines; D007204:Indium; D010165:Palladium