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Palladium‐Catalyzed Synthesis of Aryl Ketones from Boronic Acids and Carboxylic Acids Activated in situ by Pivalic Anhydride
Author(s) -
Gooßen Lukas J.,
Ghosh Keya
Publication year - 2002
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 - 10.1002/1099-0690(200210)2002:19<3254::aid-ejoc3254>3.0.co;2-6
Subject(s) - chemistry , palladium , pivalic acid , catalysis , aryl , organic chemistry , ketone , carboxylic acid , acid anhydride , combinatorial chemistry , alkyl , epoxy
A new palladium‐catalyzed cross‐coupling reaction between arylboronic acids and mixed anhydrides, generated in situ from carboxylic acids and pivalic anhydride, is presented. Optimization of the new catalyst and the reaction conditions led to the development of a convenient one‐pot ketone synthesis directly from carboxylic and boronic acids in the presence of different (phosphane)palladium complexes in wet THF at 60 °C. Systematic studies were performed to elucidate the reaction mechanism of this transformation. The scope and the limitations of the new process are demonstrated by the synthesis of 33 functionalized ketones. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)