jo9b01362_si_002.cif (534.01 kB)
Selective Removal of Aminoquinoline Auxiliary by IBX Oxidation
dataset
posted on 2019-06-06, 00:00 authored by Zhiguo Zhang, Xiang Li, Mengmeng Song, Yameng Wan, Dan Zheng, Guisheng Zhang, Gong Chen8-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.
