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Updated: Apr 13, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Regioselective decarboxylative cross-coupling of carboxy isoquinoline N-oxides
Jean-Baptiste E Y Rouchet1, Cédric Schneider1, Corinne Fruit1
1Normandie University, COBRA, UMR 6014 et FR 3038, University Rouen, INSA Rouen, CNRS, IRCOF, 1 rue Tesnière, Mont-Saint-Aignan 76821 Cedex, France.
Abstract:
A straightforward method for direct decarboxylative arylation of 1- and 3-carboxy isoquinaldic acid N-oxides with aryl iodides is reported. The reaction proceeded selectively at the carboxy function site to exclusively give the corresponding C-1 or C-3 arylated product. This methodology tolerates various aryl iodides substituted by electronically different groups. Combined with subsequent Reissert-Henze chlorination and SNAr amination, the decarboxylative arylation provides an efficient access to 1,3-functionalized isoquinoline-based antitumor agent.
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