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Literature DB >> 28156039

Acceptorless Dehydrogenation of N-Heterocycles by Merging Visible-Light Photoredox Catalysis and Cobalt Catalysis.

Ke-Han He^1,2, Fang-Fang Tan¹, Chao-Zheng Zhou¹, Gui-Jiang Zhou², Xiao-Long Yang², Yang Li¹.

Abstract

Herein, the first acceptorless dehydrogenation of tetrahydroquinolines (THQs), indolines, and other related N-heterocycles, by merging visible-light photoredox catalysis and cobalt catalysis at ambient temperature, is described. The potential applications to organic transformations and hydrogen-storage materials are demonstrated. Primary mechanistic investigations indicate that the catalytic cycle occurs predominantly by an oxidative quenching pathway.

Entities: Chemical Disease

Keywords: cobalt; dehydrogenation; heterocycles; photochemistry; reaction mechanisms

Year: 2017 PMID： 28156039 DOI： 10.1002/anie.201612486

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

17 in total

1. Iridium-based hydride transfer catalysts: from hydrogen storage to fine chemicals.

Authors: Zhiyao Lu; Valeriy Cherepakhin; Ivan Demianets; Paul J Lauridsen; Travis J Williams
Journal: Chem Commun (Camb) Date: 2018-07-10 Impact factor: 6.222

2. 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

3. Prediction of ¹⁹F NMR Chemical Shifts for Fluorinated Aromatic Compounds.

Authors: Carla Saunders; Mohammad B Khaled; Jimmie D Weaver; Dean J Tantillo
Journal: J Org Chem Date: 2018-02-26 Impact factor: 4.354

4. Photoinduced oxidative activation of electron-rich arenes: alkenylation with H₂ evolution under external oxidant-free conditions.

Authors: Xia Hu; Guoting Zhang; Faxiang Bu; Xu Luo; Kebing Yi; Heng Zhang; Aiwen Lei
Journal: Chem Sci Date: 2017-12-08 Impact factor: 9.825

Acceptorless Dehydrogenation of N-Heterocycles by Merging Visible-Light Photoredox Catalysis and Cobalt Catalysis.

1. Iridium-based hydride transfer catalysts: from hydrogen storage to fine chemicals.

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

3. Prediction of ¹⁹F NMR Chemical Shifts for Fluorinated Aromatic Compounds.

4. Photoinduced oxidative activation of electron-rich arenes: alkenylation with H₂ evolution under external oxidant-free conditions.

5. Syntheses of 3,4- and 1,4-dihydroquinazolines from 2-aminobenzylamine.

Review 6. Synthetic Strategies, Reactivity and Applications of 1,5-Naphthyridines.

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

8. Oxidative [4+2] annulation of styrenes with alkynes under external-oxidant-free conditions.

9. Acceptorless dehydrogenation and hydrogenation of N- and O-containing compounds on Pd₃Au₁(111) facets.

10. Synthesis of dihydroquinazolines from 2-aminobenzylamine: N ³ -aryl derivatives with electron-withdrawing groups.