Application of secondary alkyl halides to a domino aryl alkylation reaction for the synthesis of aromatic heterocycles.
A palladium-catalyzed, norbornene-mediated ortho-alkylation reaction of aryl iodides with secondary alkyl halides is described. Intermolecular or intramolecular ortho-alkylation proceeds in a domino process with various termination steps, generating two new carbon-carbon or carbon-nitrogen bonds in one pot, to afford an array of polycyclic heterocycles. The use of enantioenriched substrates has shown that this palladium-catalyzed reaction is stereospecific, proceeding with minimal erosion of ee.
Rudolph
Alena
A
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
Rackelmann
Nils
N
Turcotte-Savard
Marc-Olivier
MO
Lautens
Mark
M
D000478:Alkylation; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D015394:Molecular Structure; D009636:Norbornanes / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D006571:Heterocyclic Compounds; D006846:Hydrocarbons, Halogenated; D009636:Norbornanes; D011084:Polycyclic Aromatic Hydrocarbons; D010165:Palladium