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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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
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Language:English
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description 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).
doi_str_mv 10.1021/ol802349u
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title Carboxylate Directed Cross-Coupling Reactions in the Synthesis of Trisubstituted Benzoic Acids
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