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Literature DB >> 28627789

γ-Functionalizations of Amines through Visible-Light-Mediated, Redox-Neutral C-C Bond Cleavage.

Wei Shu¹, Alexandre Genoux¹, Zhaodong Li¹, Cristina Nevado¹.

Abstract

Cleavage of unstrained C-C bonds under mild, redox-neutral conditions represents a challenging endeavor which is accomplished here in the context of a flexible, visible-light-mediated, γ-functionalization of amines. In situ generated C-centered radicals are harvested in the presence of Michael acceptors, thiols and alkyl halides to efficiently form new C(sp3 )-C(sp3 ), C(sp3 )-H and C(sp3 )-Br bonds, respectively.

Entities: Chemical Species

Keywords: amines; aryl migration; photocatalysis; redox-neutral reactions; remote functionalization

Year: 2017 PMID： 28627789 DOI： 10.1002/anie.201704068

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

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Cited

16 in total

1. General, Mild, and Selective Method for Desaturation of Aliphatic Amines.

Authors: Padon Chuentragool; Marvin Parasram; Yi Shi; Vladimir Gevorgyan
Journal: J Am Chem Soc Date: 2018-02-07 Impact factor: 15.419

2. Heck Reaction of Electronically Diverse Tertiary Alkyl Halides.

Authors: Daria Kurandina; Mónica Rivas; Maxim Radzhabov; Vladimir Gevorgyan
Journal: Org Lett Date: 2018-01-05 Impact factor: 6.005

3. Aliphatic Radical Relay Heck Reaction at Unactivated C(sp³ )-H Sites of Alcohols.

Authors: Padon Chuentragool; Dongari Yadagiri; Taiki Morita; Sumon Sarkar; Marvin Parasram; Yang Wang; Vladimir Gevorgyan
Journal: Angew Chem Int Ed Engl Date: 2019-01-17 Impact factor: 15.336

4. Remote Allylation of Unactivated C(sp³)-H Bonds Triggered by Photogenerated Amidyl Radicals.

Authors: Bin Xu; Uttam K Tambar
Journal: ACS Catal Date: 2019-04-16 Impact factor: 13.084

Review 5. Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Authors: Philip R D Murray; James H Cox; Nicholas D Chiappini; Casey B Roos; Elizabeth A McLoughlin; Benjamin G Hejna; Suong T Nguyen; Hunter H Ripberger; Jacob M Ganley; Elaine Tsui; Nick Y Shin; Brian Koronkiewicz; Guanqi Qiu; Robert R Knowles
Journal: Chem Rev Date: 2021-11-23 Impact factor: 60.622

Review 6. Strategies to Generate Nitrogen-centered Radicals That May Rely on Photoredox Catalysis: Development in Reaction Methodology and Applications in Organic Synthesis.

Authors: Kitae Kwon; R Thomas Simons; Meganathan Nandakumar; Jennifer L Roizen
Journal: Chem Rev Date: 2021-10-08 Impact factor: 60.622

γ-Functionalizations of Amines through Visible-Light-Mediated, Redox-Neutral C-C Bond Cleavage.

1. General, Mild, and Selective Method for Desaturation of Aliphatic Amines.

2. Heck Reaction of Electronically Diverse Tertiary Alkyl Halides.

3. Aliphatic Radical Relay Heck Reaction at Unactivated C(sp³ )-H Sites of Alcohols.

4. Remote Allylation of Unactivated C(sp³)-H Bonds Triggered by Photogenerated Amidyl Radicals.

Review 5. Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Review 6. Strategies to Generate Nitrogen-centered Radicals That May Rely on Photoredox Catalysis: Development in Reaction Methodology and Applications in Organic Synthesis.

Review 7. Aryl Transfer Strategies Mediated by Photoinduced Electron Transfer.

8. Chiral piperidines from acyclic amines via enantioselective, radical-mediated δ C-H cyanation.

9. General, Auxiliary-Enabled Photoinduced Pd-Catalyzed Remote Desaturation of Aliphatic Alcohols.

10. Radical cascade synthesis of azoles via tandem hydrogen atom transfer.