Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 20, Pages 12792-12799Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01362
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Funding
- NSFC [U1604285, 21772032, 21702051]
- PCSIRT [IRT1061]
- 111 Project [D17007]
- Henan Provincial Natural Science Foundation [162300410180]
- Science & Technology Innovation Talents in Universities of Henan Province [17HASTIT002]
- Program for Innovative Research Team of Science and Technology in the University of Henan Province [18IRTSTHN004]
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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 alpha-amino acid (alpha AA) substrates enhances the overall synthetic utility of the AQ-directed palladium-catalyzed C-H functionalization strategy for synthesis of complex alpha AAs.
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