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A new regioselective Heck vinylation with enamides. Synthesis and investigation of fluorous-tagged bidentate ligands for fast separation by Karl S. A. Vallin; Qisheng Zhang; Mats Larhed; Dennis P. Curran; Anders Hallberg is a Chemistry article available to read on EtoBox.

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Internal ligand-controlled Heck vinylations of enamides were performed with high regioselectivity and delivered moderate to good yields of dienamides. Controlled heating by microwave irradiation accelerated the palladium-catalyzed reactions, and full conversions were achieved after reaction times of only 15-30 min. New bidentate fluorous-tagged 1,3-bis(diphenylphosphino)propane ligands (F-dppp's) were synthesized and examined. The cationic vinylations of the enamides with F-dppp ligands rendered essentially the same alpha-selectivity and catalytic activity as in those vinylations where nonfluorous ligands were employed. After reaction, the fluorous-tagged ligand material was easily removed by convenient solid fluorous phase separation. The high selectivity, simplicity, and generality of the experimental procedure should make this approach to 2-acylamino-1,3-butadienes attractive.

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Author

Karl S. A. Vallin; Qisheng Zhang; Mats Larhed; Dennis P. Curran; Anders Hallberg

Publisher

American Chemical Society (ACS)

Published

2003

Language

EN

Field

Chemistry (Physical Sciences)