Mild conditions for the synthesis of functionalized pyrrolidines via Pd-catalyzed carboamination reactions.
[reaction: see text] The palladium-catalyzed carboamination of N-protected gamma-aminoalkenes with aryl bromides and triflates has been achieved under new, mild reaction conditions using the weak base Cs(2)CO(3) in dioxane solvent. These reactions tolerate a wide variety of functional groups, including enolizable ketones, nitro groups, methyl esters, and acetates, which are not compatible with previously described conditions.
Bertrand
Myra Beaudoin
MB
Department of Chemistry, University of Michigan, 930 N. University Avenue, Ann Arbor, Michigan 48109-1055, USA.
Leathen
Matthew L
ML
Wolfe
John P
JP
D000085:Acetates / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D000586:Amination; D002254:Carbonates / Q000737:chemistry*; D002384:Catalysis; D002586:Cesium / Q000737:chemistry; D004146:Dioxanes / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D006842:Hydrocarbons, Brominated / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry; D008956:Models, Chemical; D009574:Nitro Compounds / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D011759:Pyrrolidines / Q000138:chemical synthesis*; D012997:Solvents / Q000737:chemistry
D000085:Acetates; D000475:Alkenes; D002254:Carbonates; D004146:Dioxanes; D004952:Esters; D006842:Hydrocarbons, Brominated; D007659:Ketones; D008698:Mesylates; D009574:Nitro Compounds; D011759:Pyrrolidines; D012997:Solvents; D002586:Cesium; D010165:Palladium; C025223:1,4-dioxane; C012077:trifluoromethanesulfonic acid