Intermolecular Trapping of Alkoxyl Radicals with Alkenes: A New Route to Ether Synthesis

Synlett ◽  
2019 ◽  
Vol 30 (13) ◽  
pp. 1489-1495 ◽  
Author(s):  
Anne-Laure Barthelemy ◽  
Béatrice Tuccio ◽  
Emmanuel Magnier ◽  
Guillaume Dagousset
Keyword(s):  
Hydrogen Atom ◽  
Reactive Species ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer ◽  
Photoredox Catalysis ◽  
Carbon Centered Radical ◽  
Styrene Derivatives ◽  
Ether Synthesis

Alkoxyl radicals are highly reactive species which rapidly react by hydrogen atom transfer (HAT) or β-fragmentation to afford a carbon-centered radical. We discuss herein how these RO· radicals can be efficiently trapped in an intermolecular manner by styrene derivatives when they are generated by photoredox catalysis from the corresponding N-alkoxypyridinium salts. This allows for the synthesis of valuable ethers with complete anti-Markovnikov regioselectivity.1 Introduction2 Anti-Markovnikov Alkoxylation of Alkenes: Background3 Addition of Alkoxyl Radicals to Styrenes4 Summary and Outlook

Carbonylative Coupling of Simple Alkanes and Alkenes Enabled by Organic Photoredox Catalysis

2021 ◽  
Author(s):  
Ling Chen ◽  
Jing Hou ◽  
Ming Zheng ◽  
Le-Wu Zhan ◽  
Wan-Ying Tang ◽  
...  
Keyword(s):  
Hydrogen Atom ◽  
Visible Light ◽  
Transfer Process ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer ◽  
Photoredox Catalysis ◽  
Visible Light Driven

A visible-light-driven direct carbonylative coupling of simple alkanes and alkenes via the combination of the hydrogen atom transfer process and photoredox catalysis has been demonstrated. Employing the N-alkoxyazinium salt as...

scholarly journals Dual Cobalt and Photoredox Catalysis Enabled Intermolecular Oxidative Hydrofunctionalization

2020 ◽  
Author(s):  
Han-Li Sun ◽  
Fan Yang ◽  
Wei-Ting Ye ◽  
Jun-Jie Wang ◽  
Rong Zhu
Keyword(s):  
Hydrogen Atom ◽  
Visible Light ◽  
Electrochemical Analysis ◽  
Hydrogen Atom Transfer ◽  
Redox Process ◽  
Photochemical Oxidation ◽  
Atom Transfer ◽  
Photoredox Catalysis ◽  
Wide Range ◽  
Selective Alkylation

A general protocol has been developed for the Markovnikov-selective intermolecular hydrofunctionalization based on visible-light-mediated Co/Ru dual catalysis. The key feature involves the photochemical oxidation of an organocobalt(III) intermediate derived from hydrogen atom transfer, which is supported by electrochemical analysis, quenching studies and stoichiometric experiments. This unique redox process enables the efficient branch-selective alkylation of pharmaceutically important nucleophiles (phenols, sulfonamides and various N-heterocycles) using a wide range of alkenes including moderately electron-deficient ones. Moreover, light-gated polar functionalization via organocobalt species was demonstrated.

Iminyl Radical-Triggered 1,5-Hydrogen-Atom Transfer/Heck-Type Coupling by Visible-Light Photoredox Catalysis

2019 ◽  
Vol 84 (10) ◽  
pp. 6475-6482 ◽  
Author(s):  
Li Chen ◽  
Li-Na Guo ◽  
Zhi-Yong Ma ◽  
Yu-Rui Gu ◽  
Junjie Zhang ◽  
...  
Keyword(s):  
Hydrogen Atom ◽  
Visible Light ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer ◽  
Photoredox Catalysis ◽  
Type Coupling

Organic photoredox catalyzed C–H silylation of quinoxalinones or electron-deficient heteroarenes under ambient air conditions

2021 ◽  
Author(s):  
Changhui Dai ◽  
Yanling Zhan ◽  
Ping Liu ◽  
Peipei Sun
Keyword(s):  
Hydrogen Atom ◽  
Ambient Air ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer ◽  
Photoredox Catalysis

Direct C–H silylation of quinoxalinones was achieved by the combination of organic photoredox catalysis and hydrogen atom transfer (HAT) under ambient air conditions.

scholarly journals Scalable thioarylation of unprotected peptides and biomolecules under Ni/photoredox catalysis

2018 ◽  
Vol 9 (2) ◽  
pp. 336-344 ◽  
Author(s):  
Brandon A. Vara ◽  
Xingpin Li ◽  
Simon Berritt ◽  
Christopher R. Walters ◽  
E. James Petersson ◽  
...  
Keyword(s):  
Hydrogen Atom ◽  
Visible Light ◽  
Hydrogen Atom Transfer ◽  
Cysteine Residues ◽  
Atom Transfer ◽  
Photoredox Catalysis ◽  
Ambient Conditions

A mechanistically distinct, Ni/photoredox-catalyzed arylation of unprotected, native thiols (e.g., cysteine residues) is reported – a process initiated through a visible light-promoted, hydrogen atom transfer (HAT) event under ambient conditions.

Direct C–H Multifluoroarylation of Ethers through Hydrogen Atom Transfer Using Photoredox Catalysis

2019 ◽  
Vol 84 (11) ◽  
pp. 6895-6903 ◽  
Author(s):  
Junlei Wang ◽  
Binbin Huang ◽  
Yuan Gao ◽  
Chao Yang ◽  
Wujiong Xia
Keyword(s):  
Hydrogen Atom ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer ◽  
Photoredox Catalysis

scholarly journals Dual Cobalt and Photoredox Catalysis Enabled Intermolecular Oxidative Hydrofunctionalization

2020 ◽  
Author(s):  
Han-Li Sun ◽  
Fan Yang ◽  
Wei-Ting Ye ◽  
Jun-Jie Wang ◽  
Rong Zhu
Keyword(s):  
Hydrogen Atom ◽  
Visible Light ◽  
Electrochemical Analysis ◽  
Hydrogen Atom Transfer ◽  
Redox Process ◽  
Photochemical Oxidation ◽  
Atom Transfer ◽  
Photoredox Catalysis ◽  
Wide Range ◽  
Selective Alkylation

A general protocol has been developed for the Markovnikov-selective intermolecular hydrofunctionalization based on visible-light-mediated Co/Ru dual catalysis. The key feature involves the photochemical oxidation of an organocobalt(III) intermediate derived from hydrogen atom transfer, which is supported by electrochemical analysis, quenching studies and stoichiometric experiments. This unique redox process enables the efficient branch-selective alkylation of pharmaceutically important nucleophiles (phenols, sulfonamides and various N-heterocycles) using a wide range of alkenes including moderately electron-deficient ones. Moreover, light-gated polar functionalization via organocobalt species was demonstrated.

scholarly journals Triarylamine-based porous coordination polymers performing both hydrogen atom transfer and photoredox catalysis for regioselective α-amino C(sp3)–H arylation

2021 ◽  
Author(s):  
Hanning Li ◽  
Yang Yang ◽  
Jing Xu ◽  
Cheng He ◽  
Chunying Duan
Keyword(s):  
Organic Chemistry ◽  
Hydrogen Atom ◽  
Coordination Polymer ◽  
Coordination Polymers ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer ◽  
Photoredox Catalysis ◽  
Porous Coordination Polymers ◽  
Direct Functionalization

Direct functionalization of C(sp3)–H bonds in a predictable, selective and recyclable manner has become a central challenge in modern organic chemistry. Through incorporating different triarylamine-containing ligands into one coordination polymer,...

Synthesis of Ketodeoxysugars from Acylated Pyranosides Using Photoredox Catalysis and Hydrogen Atom Transfer

ACS Catalysis ◽  
2021 ◽  
Vol 11 (17) ◽  
pp. 11171-11179
Author(s):  
Julia A. Turner ◽  
Nicholas Rosano ◽  
Daniel J. Gorelik ◽  
Mark S. Taylor
Keyword(s):  
Hydrogen Atom ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer ◽  
Photoredox Catalysis
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