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
2003; Wiley; Volume: 345; Issue: 4 Linguagem: Inglês
10.1002/adsc.200390062
ISSN1615-4169
AutoresMahavir Prashad, Yugang Liu, Oljan Repič,
Tópico(s)Catalytic C–H Functionalization Methods
ResumoAbstract An efficient and large‐scale synthesis of 1‐(4‐chlorophenyl)‐3,3‐dimethyl‐2‐butanone ( 1 ) by an α‐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.
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