Efficient, regioselective palladium-catalyzed tandem Heck-isomerization reaction of aryl bromides and non-allylic benzyl alcohols.
An efficient and mild method to couple aryl bromides and activated non-allylic alcohols in a Heck reaction with tandem isomerization to selectively afford high yields of 1,5-diarylalkan-1-ones has been developed. Mechanistic insight was gained through NMR studies of products derived from deuterium-labeled intermediates.
Crawley
Matthew L
ML
Discovery Medicinal Chemistry, Chemical Sciences, Wyeth Research, 500 Arcola Road, Collegeville, Pennsylvania 19426, USA. crawlem@wyeth.com
Phipps
Kristin M
KM
Goljer
Igor
I
Mehlmann
John F
JF
Lundquist
Joseph T
JT
Ullrich
John W
JW
Yang
Cuijian
C
Mahaney
Paige E
PE
D001592:Benzyl Alcohols / Q000737:chemistry*; D001965:Bromides / Q000737:chemistry*; D002384:Catalysis; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D001592:Benzyl Alcohols; D001965:Bromides; D010165:Palladium