@article{pittir20459, volume = {68}, number = {17}, month = {September}, author = {KSA Vallin and Q Zhang and M Larhed and DP Curran and A Hallberg}, title = {A new regioselective Heck vinylation with enamides. Synthesis and investigation of fluorous-tagged bidentate ligands for fast separation}, journal = {Journal of Organic Chemistry}, pages = {6639 -- 6645}, year = {2003}, url = {http://d-scholarship-dev.library.pitt.edu/20459/}, abstract = {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 {\ensuremath{\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.} }