Palladium-catalyzed alkoxyamination of alkenes with use of N-fluorobenzenesulfonimide as oxidant.
A Pd-catalyzed alkoxyamination of protected aminoalkenes promoted by N-fluorobenzenesulfonimide is described. This mild transformation allows the direct formation of ethers from carbon-carbon double bonds. An unusual switch from exo to endo selectivity in polar solvents was discovered, allowing the selective formation of either regioisomer by careful choice of reaction conditions.
Liskin
Dmitry V
DV
Department of Chemistry, University of Washington, Box 351700, Seattle, Washington 98195-1700, USA.
Sibbald
Paul A
PA
Rosewall
Carolyn F
CF
Michael
Forrest E
FE
D000475:Alkenes / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D003500:Cyclization; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*; D000096926:Benzenesulfonamides
D000475:Alkenes; D004987:Ethers; D010165:Palladium; D013449:Sulfonamides; C523711:N-fluorobenzenesulfonimide; D000096926:Benzenesulfonamides