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Highly Chemoselective Deoxygenation of N-Heterocyclic N-Oxides Using Hantzsch Esters as Mild Reducing Agents

Ju Hyeon An, Kyu Dong Kim and Jun Hee Lee*

*Department of Advanced Materials Chemistry, Dongguk University, Gyeongju Campus, Gyeongju 38066, Republic of Korea, Email: leejunheedongguk.ac.kr

J. H. An, K. D. Kim, J. H. Lee, J. Org. Chem., 2021, 86, 2876-2894.

DOI: 10.1021/acs.joc.0c02805 (free Supporting Information)


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Abstract

Visible light-mediated metallaphotoredox catalysis enables a highly chemoselective deoxygenation of N-heterocyclic N-oxides using Hantzsch esters as the stoichiometric reductants and only a tiny amount of the catalyst within a few minutes at room temperature. The reaction tolerates a wide range of functional groups, such as carbamates, esters, ketones, nitrile groups, nitro groups, and halogens.

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Visible-Light Photocatalyzed Deoxygenation of N-Heterocyclic N-Oxides

K. D. Kim, J. H. Lee, Org. Lett., 2018, 20, 7712-7716.


Key Words

quinolines, deoxygenation of N-oxides, Hantzsch esters


ID: J42-Y2021