Carboxylate Directed Cross-Coupling Reactions in the Synthesis of Trisubstituted Benzoic Acids

The carboxylate anion has been used as a directing group to effect selective ortho-substituted derivatives 3 (>99:1 selectivity 50−80% yield). The solvent, base, and equivalents of base are the determining factors for the success of this reaction. The directing effect can be reversed by the appro...

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Bibliographic Details
Published in:Organic letters 2008-12, Vol.10 (24), p.5601-5604
Main Authors: Houpis, Ioannis N, Huang, Changkang, Nettekoven, Ulrike, Chen, Jason G, Liu, Renmao, Canters, Martine
Format: Article
Language:English
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Summary:The carboxylate anion has been used as a directing group to effect selective ortho-substituted derivatives 3 (>99:1 selectivity 50−80% yield). The solvent, base, and equivalents of base are the determining factors for the success of this reaction. The directing effect can be reversed by the appropriate use of phosphine ligands to prepare the para-substituted 4 selectively (ca. 12:1 selectivity).
ISSN:1523-7060
1523-7052
DOI:10.1021/ol802349u