An annulative approach to highly substituted indoles: unusual effect of phenolic additives on the success of the arylation of ketone enolates.
A novel palladium-catalyzed arylation of ketone enolates with o-nitrohaloarenes was achieved through the addition of phenol additives. The mild reaction conditions employed allowed for the inclusion of a wide variety of functional groups in both substrates to be tolerated. The products of this reaction were then readily reductively cyclized to give highly substituted indoles in moderate to excellent overall yields.
Rutherford
Jennifer L
JL
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Rainka
Matthew P
MP
Buchwald
Stephen L
SL
D001555:Benzene Derivatives / Q000737:chemistry; D001969:Bromobenzenes / Q000737:chemistry; D002384:Catalysis; D006846:Hydrocarbons, Halogenated / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis*; D007659:Ketones / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D010636:Phenols / Q000737:chemistry*
D001555:Benzene Derivatives; D001969:Bromobenzenes; D006846:Hydrocarbons, Halogenated; D007211:Indoles; D007659:Ketones; D009942:Organometallic Compounds; D010636:Phenols; D010165:Palladium; C032036:bromobenzene