Palladium-Catalyzed Alkoxyamination of Alkenes with Use of N-Fluorobenzenesulfonimide as Oxidant

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...

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Veröffentlicht in:Journal of organic chemistry 2010-09, Vol.75 (18), p.6294-6296
Hauptverfasser: Liskin, Dmitry V, Sibbald, Paul A, Rosewall, Carolyn F, Michael, Forrest E
Format: Artikel
Sprache:eng
Schlagworte:
Alkenes - chemistry
Amination
Catalysis
Chemistry
Cyclization
Ethers - chemical synthesis
Ethers - chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Molecular Structure
Organic chemistry
Oxidation-Reduction
Palladium - chemistry
Preparations and properties
Stereoisomerism
Sulfonamides - chemistry
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo101171g