Palladium-catalyzed arylation of ketone enolates: an expeditious entry to tamoxifen-related 1,2,2-triarylethanones.
[reaction: see text]. After a rigorous study on the effect of several catalytic systems, a simple, high yielding procedure for the preparation of 1,2,2-triarylethanones, skeletal analogues of tamoxifen, is presented. Apart from the economic and environmental advantages involved, this palladium-catalyzed arylation of deoxybenzoin enolates features a lack of ortho-arylation side reactions. In addition, an alternative approach from acetophenones to the target triarylethanone system is also announced.
Churruca
Fátima
F
Kimika Organikoa II Saila, Zientzi Fakultatea, Euskal Herriko Unibertsitatea, P.O. Box 644, 48080 Bilbao, Spain.
SanMartin
Raul
R
Tellitu
Imanol
I
Domínguez
Esther
E
D000478:Alkylation; D018931:Antineoplastic Agents, Hormonal / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007202:Indicators and Reagents; D007659:Ketones / Q000737:chemistry; D010165:Palladium; D013629:Tamoxifen / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
D018931:Antineoplastic Agents, Hormonal; D007202:Indicators and Reagents; D007659:Ketones; D013629:Tamoxifen; D010165:Palladium