Regioselective access to substituted oxindoles via rhodium-catalyzed carbene C–H insertion

D Gauthier, RH Dodd, P Dauban

Index: Gauthier, Delphine; Dodd, Robert H.; Dauban, Philippe Tetrahedron, 2009 , vol. 65, # 41 p. 8542 - 8555

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Citation Number: 14

Abstract

Rhodium-catalyzed decomposition of diazoamides followed by insertion of the resulting carbenes into an aromatic C–H bond gives access to substituted oxindoles. The reaction takes place with aromatic rings substituted by either electron-donating or-withdrawing groups at ortho, meta or para positions and the regioselectivity can be controlled by a substitution α to the diazo functionality. In the presence of an ester, the reaction leads to ...