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.

Polyphenylalkane derivatives Q 0720 Efficient, Regioselective Palladium-Catalyzed Tandem Heck-Isomerization Reaction of Aryl Bromides and Non-Allylic Benzyl Alcohols. -The reaction proceeds without any ligand and affords the 1,5-diarylalkanones with high and 1,4-diarylalkanones with low yields. -(CRAWLEY*, M. L.; PHIPPS, K. M.; GOLJER, I.; MEHLMANN, J. F.; LUNDQUIST, J. T.; ULLRICH, J. W.; YANG, C.; MAHANEY, P. E.; Org. Lett. 11 (2009) 5, 1183-1185; Discovery Med. Chem., Wyeth Res. Ltd., Collegeville, PA 19426, USA; Eng.) -R. Steudel 30-090