Development of an anomalous Heck reaction: skeletal rearrangement of divinyl and enyne carbinols.
[reaction: see text] A general set of conditions that achieves the union of aryl halides and divinyl or enyne carbinols to afford tri- or tetrasubstituted olefins in good yields (up to 83%) is described. The mechanism by which this proceeds is believed to involve the intermediacy of a cyclopropanol, followed by a novel skeletal reorganization. The ability to suppress beta-hydride elimination of organopalladium intermediates appears to be critical to the success of these processes.
Ndungu
J Maina
JM
Department of Chemistry, University of California, Berkeley, California 94720, USA.
Larson
Kimberly K
KK
Sarpong
Richmond
R