Direct boronation of allyl alcohols with diboronic acid using palladium pincer-complex catalysis. A remarkably facile allylic displacement of the hydroxy group under mild reaction conditions.
Allyl alcohols were converted to allyl boronic acids and subsequently to trifluoro(allyl)borates with tetrahydroxy diboron using palladium pincer-complex catalysis. These reactions are regio- and stereoselective proceeding with high isolated yields. Competitive boronation experiments indicate that under the applied reaction conditions the allylic displacement of a hydroxy group is faster than the displacement of an acetate leaving group. It is assumed that the hydroxy group of the allyl alcohol is converted to a diboronic acid ester functionality, which can easily be substituted.
Olsson
Vilhelm J
VJ
Department of Organic Chemistry, Stockholm University, SE-106 91 Stockholm, Sweden.
Sebelius
Sara
S
Selander
Nicklas
N
Szabó
Kalman J
KJ