Synthesis of pyrrolidines via palladium(II)-catalyzed aerobic oxidative carboamination of butyl vinyl ether and styrenes with allyl tosylamides.
[Structure: see text] Palladium(II) catalyzes the oxidative coupling of allyl tosylamides with butyl vinyl ether and various styrene derivatives to produce 2,4-substituted pyrrolidine products at room temperature. Molecular oxygen together with a copper(II) cocatalyst mediates reoxidation of the palladium catalyst. The reactions with styrene substrates can be performed in an open flask with ambient air as the source of O2. Several nontraditional cocatalysts, including catechol, cyclooctadiene, and methyl acrylate, have a beneficial effect on the reactions.
Scarborough
Christopher C
CC
University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, USA.
Stahl
Shannon S
SS
D000498:Allyl Compounds / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D011759:Pyrrolidines / Q000138:chemical synthesis*; D013343:Styrenes / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
D000498:Allyl Compounds; D000577:Amides; D011759:Pyrrolidines; D013343:Styrenes; D014753:Vinyl Compounds; C100195:vinyl ether; D010165:Palladium