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Palladium‐Catalysed Direct Arylation of Heteroaromatics Bearing Unprotected Hydroxyalkyl Functions using Aryl Bromides
Author(s) -
Roger Julien,
Požgan Franc,
Doucet Henri
Publication year - 2010
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.200900793
Subject(s) - chemistry , palladium , aryl , catalysis , potassium carbonate , medicinal chemistry , organic chemistry , ether , selectivity , combinatorial chemistry , alkyl
Heteroaromatics bearing unprotected hydroxyalkyl functions can be arylated using aryl or heteroaryl bromides, via palladium‐catalysed carbon‐hydrogen bond activation/arylation. Good yields were generally obtained using 0.01–0.5 mol% of the air‐stable palladium acetate complex as the catalyst. The nature of the base was found to be crucial for the selectivity of this reaction. Potassium acetate led to the direct arylation products whereas caesium carbonate led to the formation of the ether. This procedure is certainly more atom‐economic than other methods for the preparation of such compounds, as no protection/deprotection sequence of the hydroxyalkyl function and no preparation of an organometallic derivative is required.