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Palladium‐Catalyzed Elimination/Isomerization of Enol Triflates into 1,3‐Dienes
Author(s) -
Crouch Ian T.,
Dreier Timothy,
Frantz Doug E.
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201101820
Subject(s) - isomerization , allene , palladium , enol , chemistry , cationic polymerization , catalysis , hydride , medicinal chemistry , photochemistry , organic chemistry , hydrogen
Dying to be Dienes: Substituted 1,3‐dienes were synthesized by the title reaction (see scheme; Tf=trifluoromethanesulfonyl). Preliminary studies support a mechanistically distinct pathway that involves an initial β‐hydride elimination from a cationic vinyl palladium(II) intermediate, a subsequent regiospecific hydropalladation of the corresponding allene intermediate, and a final β‐hydride elimination.