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Suzuki–Miyaura Coupling Reaction of Boronic Acids and Ethyl Glyoxylate: Synthetic Access to Mandelate Derivatives
Author(s) -
Francesco Irene Notar,
Wagner Alain,
Colobert Françoise
Publication year - 2008
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.200800881
Subject(s) - chemistry , glyoxylate cycle , mandelic acid , catalysis , palladium , coupling reaction , organic chemistry , combinatorial chemistry , base (topology) , suzuki reaction , medicinal chemistry , enzyme , mathematical analysis , mathematics
The palladium‐catalyzed coupling reaction of arylboronicacids with ethyl glyoxylate provides a straightforward method for the synthesis of mandelic esters. Pd 2 (dba) 3 · CHCl 3 in combination with 2‐di‐ tert ‐butylphosphanylbiphenyl as the catalytic system and Cs 2 CO 3 as the base were used. The reaction tolerates a wide range of functionalized boronicacids. Mandelic esters were isolated in good‐to‐excellent yields with a variety of neutral, slightly electron‐rich, and slightly electron‐poor substituents.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)