An expeditious synthesis of 1-(4-chlorophenyl)-3,3-dimethyl-2-butanone by a ligand-free palladium-catalyzed α-arylation of pinacolone:: Scale-up and effect of base concentration

被引：13

作者：

Prashad, M ^{[1
]}

Liu, YG ^{[1
]}

Repic, O ^{[1
]}

机构：

[1] Novartis Inst Biomed Res, Proc Res & Dev, Chem & Analyt Dev, E Hanover, NJ 07936 USA

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2003年 / 345卷 / 04期

关键词：

alpha-arylation; ketones; ligand-free homogeneous catalysis; palladium; pinacolone;

D O I：

10.1002/adsc.200390062

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An efficient and large-scale synthesis of I(4-chlorophenyl)-3,3-dimethyl-2-butanone (1) by an alpha-arylation of pinacolone (2) with 1-bromo-4-chlorobenzene (3) in the presence of palladium acetate and sodium t-butoxide in toluene is described. An increase in the concentration of sodium t-butoxide to 2.5 - 3.0 equivalents suppressed the formation of over-arylated products. These ligand-free conditions afforded a yield of 1 that was comparable to those obtained by using a ligand.

引用

页码：533 / 536

页数：4

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