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Palladium‐Catalyzed Direct Arylation of 4‐Chromanones: Selective Synthesis of Racemic Isoflavanones and 3,3‐Diaryl‐4‐chromanones
Author(s) -
Bellina Fabio,
Masini Tiziana,
Rossi Renzo
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901356
Subject(s) - chemistry , catalysis , palladium , aryl , selectivity , organic chemistry , combinatorial chemistry , alkyl
For the first time, the synthesis of racemic isoflavanones has been achieved in satisfactory to good yields and with high selectivity by Pd‐catalyzed direct C‐3 arylation of 3‐unsubstituted 4‐chromanones with aryl bromides with the aid of a Pd 2 (dba) 3 / t Bu 3 PHBF 4 catalyst system in the presence of KHCO 3 as the base in a dioxane/water mixture (4:1). This catalyst system has also been employed in an unprecedented synthesis of 3,3‐diaryl‐4‐chromanones through direct arylation of 4‐chromanones in water.