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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
Author(s) -
Prashad Mahavir,
Liu Yugang,
Repič Oljan
Publication year - 2003
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200390062
Subject(s) - chemistry , butanone , ligand (biochemistry) , chlorobenzene , palladium , yield (engineering) , base (topology) , toluene , catalysis , organic chemistry , medicinal chemistry , solvent , mathematical analysis , biochemistry , materials science , receptor , mathematics , metallurgy
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.