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

Kyu Dong Kim, Jun Hee Lee*

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

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

DOI: 10.1021/acs.orglett.8b03446 (free Supporting Information)


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Abstract

Visible-light mediates a scalable and operationally simple method for the chemoselective deoxygenation of a wide range of N-heterocyclic N-oxides at room temperature using only commercially available reagents. This protocol offers an unprecedented chemoselective removal of the oxygen atom in a quinoline N-oxide in the presence of a pyridine N-oxide through the judicious selection of the photocatalyst.

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

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


Key Words

deoxygenation of aza-aromatics, quinolines, hydrazine, photochemistry


ID: J54-Y2018