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Literature DB >> 28805268

Organo-Photoredox Catalyzed Oxidative Dehydrogenation of N-Heterocycles.

Manoj K Sahoo¹, Garima Jaiswal¹, Jagannath Rana¹, Ekambaram Balaraman¹.

Abstract

We report here for the first time the catalytic oxidative dehydrogenation of N-heterocycles by a visible-light organo-photoredox catalyst with low catalyst loading (0.1-1 mol %). The reaction proceeds efficiently under base- and additive-free conditions with ambient air at room temperature. The utility of this benign approach is demonstrated by the synthesis of various pharmaceutically relevant N-heteroarenes such as quinoline, quinoxaline, quinazoline, acridine, and indole.

Entities: Chemical Disease

Keywords: heterocycles; homogeneous catalysis; oxidative dehydrogenation; quinoline; synthetic methods

Year: 2017 PMID： 28805268 DOI： 10.1002/chem.201703642

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

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Cited

8 in total

1. Visible-Light-Promoted Iridium(III)-Catalyzed Acceptorless Dehydrogenation of N-Heterocycles at Room Temperature.

Authors: Carmen Mejuto; Laura Ibáñez-Ibáñez; Gregorio Guisado-Barrios; Jose A Mata
Journal: ACS Catal Date: 2022-05-10 Impact factor: 13.700

2. Visible-light-induced C(sp³)-H activation for a C-C bond forming reaction of 3,4-dihydroquinoxalin-2(1H)-one with nucleophiles using oxygen with a photoredox catalyst or under catalyst-free conditions.

Authors: Pavan Sudheer Akula; Bor-Cherng Hong; Gene-Hsiang Lee
Journal: RSC Adv Date: 2018-05-29 Impact factor: 4.036

3. Synthesis of Xanthones, Thioxanthones and Acridones by a Metal-Free Photocatalytic Oxidation Using Visible Light and Molecular Oxygen.

Authors: Alejandro Torregrosa-Chinillach; Rafael Chinchilla
Journal: Molecules Date: 2021-02-12 Impact factor: 4.411

4. Photocatalytic Aerobic Dehydrogenation of N-Heterocycles with Ir(III) Photosensitizers Bearing the 2(2'-Pyridyl)benzimidazole Scaffold.

Authors: Igor Echevarría; Mónica Vaquero; Blanca R Manzano; Félix A Jalón; Roberto Quesada; Gustavo Espino
Journal: Inorg Chem Date: 2022-04-08 Impact factor: 5.436

Review 8. Visible Light-Induced Aerobic Oxidative Dehydrogenation of C-N/C-O to C=N/C=O Bonds Using Metal-Free Photocatalysts: Recent Developments.

Authors: Alejandro Torregrosa-Chinillach; Rafael Chinchilla
Journal: Molecules Date: 2022-01-13 Impact factor: 4.411

8 in total

Organo-Photoredox Catalyzed Oxidative Dehydrogenation of N-Heterocycles.

1. Visible-Light-Promoted Iridium(III)-Catalyzed Acceptorless Dehydrogenation of N-Heterocycles at Room Temperature.

2. Visible-light-induced C(sp³)-H activation for a C-C bond forming reaction of 3,4-dihydroquinoxalin-2(1H)-one with nucleophiles using oxygen with a photoredox catalyst or under catalyst-free conditions.

3. Synthesis of Xanthones, Thioxanthones and Acridones by a Metal-Free Photocatalytic Oxidation Using Visible Light and Molecular Oxygen.

4. Photocatalytic Aerobic Dehydrogenation of N-Heterocycles with Ir(III) Photosensitizers Bearing the 2(2'-Pyridyl)benzimidazole Scaffold.

Review 5. Recent applications of Rose Bengal catalysis in N-heterocycles: a short review.

6. Iodine-catalyzed convergent aerobic dehydro-aromatization toward benzazoles and benzazines.

7. Synthesis of N-aryl amines enabled by photocatalytic dehydrogenation.

Review 8. Visible Light-Induced Aerobic Oxidative Dehydrogenation of C-N/C-O to C=N/C=O Bonds Using Metal-Free Photocatalysts: Recent Developments.

Organo-Photoredox Catalyzed Oxidative Dehydrogenation of N-Heterocycles.

1. Visible-Light-Promoted Iridium(III)-Catalyzed Acceptorless Dehydrogenation of N-Heterocycles at Room Temperature.

2. Visible-light-induced C(sp3)-H activation for a C-C bond forming reaction of 3,4-dihydroquinoxalin-2(1H)-one with nucleophiles using oxygen with a photoredox catalyst or under catalyst-free conditions.

3. Synthesis of Xanthones, Thioxanthones and Acridones by a Metal-Free Photocatalytic Oxidation Using Visible Light and Molecular Oxygen.

4. Photocatalytic Aerobic Dehydrogenation of N-Heterocycles with Ir(III) Photosensitizers Bearing the 2(2'-Pyridyl)benzimidazole Scaffold.

Review 5. Recent applications of Rose Bengal catalysis in N-heterocycles: a short review.

6. Iodine-catalyzed convergent aerobic dehydro-aromatization toward benzazoles and benzazines.

7. Synthesis of N-aryl amines enabled by photocatalytic dehydrogenation.

Review 8. Visible Light-Induced Aerobic Oxidative Dehydrogenation of C-N/C-O to C=N/C=O Bonds Using Metal-Free Photocatalysts: Recent Developments.

2. Visible-light-induced C(sp³)-H activation for a C-C bond forming reaction of 3,4-dihydroquinoxalin-2(1H)-one with nucleophiles using oxygen with a photoredox catalyst or under catalyst-free conditions.