scholarly journals Brønsted Base Assisted Photoredox Catalysis: Proton Coupled Electron Transfer for Remote C−C Bond Formation via Amidyl Radicals

2018 ◽  
Vol 24 (53) ◽  
pp. 14054-14058 ◽  
Author(s):  
Jiaqi Jia ◽  
Yee Ann Ho ◽  
Raoul F. Bülow ◽  
Magnus Rueping
Keyword(s):  
Electron Transfer ◽  
Bond Formation ◽  
Photoredox Catalysis ◽  
Proton Coupled Electron Transfer ◽  
Brønsted Base

scholarly journals Chemistry With N-Centered Radicals Generated by Single-Electron Transfer-Oxidation Using Photoredox Catalysis

CCS Chemistry ◽  
2019 ◽  
pp. 38-49 ◽  
Author(s):  
Heng Jiang ◽  
Armido Studer
Keyword(s):  
Electron Transfer ◽  
Recent Literature ◽  
Bond Cleavage ◽  
Photoredox Catalysis ◽  
Proton Coupled Electron Transfer ◽  
Cascade Processes ◽  
Reactive N ◽  
Radical Generation ◽  
Cleavage Reactions ◽  
Oxidative Generation

This review covers the recent literature on oxidative generation of N-centered radicals using photoredox catalysis. The concept of proton-coupled electron transfer is briefly discussed. Applications of such reactive N-centered radicals in cascade processes comprising arene amidation, alkene amidation, C—C bond cleavage reactions, and remote C—H functionalization are addressed. In addition, novel reagents allowing for clean oxidative N-radical generation are discussed.

scholarly journals N–H Bond Formation in a Manganese(V) Nitride Yields Ammonia by Light-Driven Proton-Coupled Electron Transfer

2019 ◽  
Vol 141 (12) ◽  
pp. 4795-4799 ◽  
Author(s):  
Dian Wang ◽  
Florian Loose ◽  
Paul J. Chirik ◽  
Robert R. Knowles
Keyword(s):  
Electron Transfer ◽  
Bond Formation ◽  
Proton Coupled Electron Transfer

scholarly journals Stepwise N–H bond formation from N2-derived iron nitride, imide and amide intermediates to ammonia

2016 ◽  
Vol 7 (9) ◽  
pp. 5736-5746 ◽  
Author(s):  
K. Cory MacLeod ◽  
Sean F. McWilliams ◽  
Brandon Q. Mercado ◽  
Patrick L. Holland
Keyword(s):  
Electron Transfer ◽  
Bond Formation ◽  
Iron Complexes ◽  
Spectroscopic Characterization ◽  
Iron Nitride ◽  
Proton Coupled Electron Transfer

The pathway from N2to NH3at low-coordinate iron complexes is shown through crystallographic and spectroscopic characterization of intermediates, including bridging nitride, imide, and amides. Proton-coupled electron transfer plays a key role in the transformations.

Enantioselective Photoredox Catalysis Enabled by Proton-Coupled Electron Transfer: Development of an Asymmetric Aza-Pinacol Cyclization

2013 ◽  
Vol 135 (47) ◽  
pp. 17735-17738 ◽  
Author(s):  
Lydia J. Rono ◽  
Hatice G. Yayla ◽  
David Y. Wang ◽  
Michael F. Armstrong ◽  
Robert R. Knowles
Keyword(s):  
Electron Transfer ◽  
Photoredox Catalysis ◽  
Proton Coupled Electron Transfer

Catalytic Hydroetherification of Unactivated Alkenes Enabled by Proton-Coupled Electron Transfer

2020 ◽  
Author(s):  
Elaine Tsui ◽  
Anthony J. Metrano ◽  
Yuto Tsuchiya ◽  
Robert Knowles
Keyword(s):  
Electron Transfer ◽  
Functional Group ◽  
Cyclic Ether ◽  
Hydrogen Atom Transfer ◽  
Diverse Range ◽  
Electron Transfer Mechanism ◽  
Co Catalyst ◽  
Alkoxy Radicals ◽  
Proton Coupled Electron Transfer ◽  
Brønsted Base

We report a light-driven, catalytic protocol for the intramolecular hydroetherification of unactivated alkenols to furnish cyclic ether products. These reactions occur under visible light irradiation in the presence of an Ir(III)-based photosensitizer, a Brønsted base catalyst, and a hydrogen atom transfer co-catalyst. Reactive alkoxy radicals are proposed as key intermediates that are generated by direct homolytic activation of alcohol O–H bonds through a proton-coupled electron transfer mechanism. This method exhibits a broad substrate scope and high functional group tolerance, and it accommodates a diverse range of alkene substitution patterns. Results demonstrating the extension of this catalytic system to carboetherification reactions are also presented.

ChemInform Abstract: Enantioselective Photoredox Catalysis Enabled by Proton-Coupled Electron Transfer: Development of an Asymmetric Aza-Pinacol Cyclization.

ChemInform ◽  
2014 ◽  
Vol 45 (23) ◽  
pp. no-no
Author(s):  
Lydia J. Rono ◽  
Hatice G. Yayla ◽  
David Y. Wang ◽  
Michael F. Armstrong ◽  
Robert R. Knowles
Keyword(s):  
Electron Transfer ◽  
Photoredox Catalysis ◽  
Proton Coupled Electron Transfer

Catalytic Hydroetherification of Unactivated Alkenes Enabled by Proton-Coupled Electron Transfer

2020 ◽  
Author(s):  
Elaine Tsui ◽  
Anthony J. Metrano ◽  
Yuto Tsuchiya ◽  
Robert Knowles
Keyword(s):  
Electron Transfer ◽  
Functional Group ◽  
Cyclic Ether ◽  
Hydrogen Atom Transfer ◽  
Diverse Range ◽  
Electron Transfer Mechanism ◽  
Co Catalyst ◽  
Alkoxy Radicals ◽  
Proton Coupled Electron Transfer ◽  
Brønsted Base

We report a light-driven, catalytic protocol for the intramolecular hydroetherification of unactivated alkenols to furnish cyclic ether products. These reactions occur under visible light irradiation in the presence of an Ir(III)-based photosensitizer, a Brønsted base catalyst, and a hydrogen atom transfer co-catalyst. Reactive alkoxy radicals are proposed as key intermediates that are generated by direct homolytic activation of alcohol O–H bonds through a proton-coupled electron transfer mechanism. This method exhibits a broad substrate scope and high functional group tolerance, and it accommodates a diverse range of alkene substitution patterns. Results demonstrating the extension of this catalytic system to carboetherification reactions are also presented.

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