19143-28-3Relevant articles and documents
Selective Removal of Aminoquinoline Auxiliary by IBX Oxidation
Zhang, Zhiguo,Li, Xiang,Song, Mengmeng,Wan, Yameng,Zheng, Dan,Zhang, Guisheng,Chen, Gong
, p. 12792 - 12799 (2019/07/03)
8-Aminoquinoline (AQ) is a widely used bidentate auxiliary in metal-catalyzed directed C-H functionalization reactions. Herein, we report an efficient and chemoselective method to convert various N-quinolyl carboxamides to primary amides with the treatment of a stoichiometric amount of 2-iodoxybenzoic acid oxidant or the combination of a catalytic amount of 2-iodobenzoic acid and Oxone co-oxidant in mixed solvents of H2O and HFIP. Its unique compatibility with the Phth-protected α-amino acid (αAA) substrates enhances the overall synthetic utility of the AQ-directed palladium-catalyzed C-H functionalization strategy for synthesis of complex αAAs.