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Literature DB >> 27862775

Photocatalytic C-C Bond Cleavage and Amination of Cycloalkanols by Cerium(III) Chloride Complex.

Jing-Jing Guo¹, Anhua Hu¹, Yilin Chen¹, Jianfeng Sun¹, Haoming Tang¹, Zhiwei Zuo¹.

Abstract

A general strategy for the cleavage and amination of C-C bonds of cycloalkanols has been achieved through visible-light-induced photoredox catalysis utilizing a cerium(III) chloride complex. This operationally simple methodology has been successfully applied to a wide array of unstrained cyclic alcohols, and represents the first example of catalytic C-C bond cleavage and functionalization of unstrained secondary cycloalkanols.

Entities: Chemical

Keywords: C−C bond cleavage; alcohols; amination; cerium; photochemistry

Year: 2016 PMID： 27862775 DOI： 10.1002/anie.201609035

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

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Cited

15 in total

1. A Redox Strategy for Light-Driven, Out-of-Equilibrium Isomerizations and Application to Catalytic C-C Bond Cleavage Reactions.

Authors: Eisuke Ota; Huaiju Wang; Nils Lennart Frye; Robert R Knowles
Journal: J Am Chem Soc Date: 2019-01-15 Impact factor: 15.419

2. Development of a Terpene Feedstock-Based Oxidative Synthetic Approach to the Illicium Sesquiterpenes.

Authors: Kevin Hung; Matthew L Condakes; Luiz F T Novaes; Stephen J Harwood; Takahiro Morikawa; Zhi Yang; Thomas J Maimone
Journal: J Am Chem Soc Date: 2019-02-11 Impact factor: 15.419

3. C-C Bond Cleavage Approach to Complex Terpenoids: Development of a Unified Total Synthesis of the Phomactins.

Authors: Paul R Leger; Yusuke Kuroda; Stanley Chang; Justin Jurczyk; Richmond Sarpong
Journal: J Am Chem Soc Date: 2020-08-31 Impact factor: 15.419

Review 4. Recent Advances in Photoredox-Mediated Radical Conjugate Addition Reactions: An Expanding Toolkit for the Giese Reaction.

Authors: Anastasia L Gant Kanegusuku; Jennifer L Roizen
Journal: Angew Chem Int Ed Engl Date: 2021-07-21 Impact factor: 16.823

Photocatalytic C-C Bond Cleavage and Amination of Cycloalkanols by Cerium(III) Chloride Complex.

1. A Redox Strategy for Light-Driven, Out-of-Equilibrium Isomerizations and Application to Catalytic C-C Bond Cleavage Reactions.

2. Development of a Terpene Feedstock-Based Oxidative Synthetic Approach to the Illicium Sesquiterpenes.

3. C-C Bond Cleavage Approach to Complex Terpenoids: Development of a Unified Total Synthesis of the Phomactins.

Review 4. Recent Advances in Photoredox-Mediated Radical Conjugate Addition Reactions: An Expanding Toolkit for the Giese Reaction.

5. First use of a divalent lanthanide for visible-light-promoted photoredox catalysis.

6. Silver-catalyzed remote Csp³-H functionalization of aliphatic alcohols.

7. Luminescent tungsten(vi) complexes as photocatalysts for light-driven C-C and C-B bond formation reactions.

8. Metal-free alcohol-directed regioselective heteroarylation of remote unactivated C(sp³)-H bonds.

9. Photoinduced Remote Functionalisations by Iminyl Radical Promoted C-C and C-H Bond Cleavage Cascades.

10. Visible light-promoted ring-opening functionalization of unstrained cycloalkanols via inert C-C bond scission.