TY  - JOUR
ID  - pittir20459
UR  - http://d-scholarship-dev.library.pitt.edu/20459/
IS  - 17
A1  - Vallin, KSA
A1  - Zhang, Q
A1  - Larhed, M
A1  - Curran, DP
A1  - Hallberg, A
Y1  - 2003/09/01/
N2  - 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 ?-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.
JF  - Journal of Organic Chemistry
VL  - 68
SN  - 0022-3263
TI  - A new regioselective Heck vinylation with enamides. Synthesis and investigation of fluorous-tagged bidentate ligands for fast separation
SP  - 6639 
AV  - public
EP  -  6645
ER  -