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

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.

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.

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.

Remote C–C bond formation via visible light photoredox-catalyzed intramolecular hydrogen atom transfer

2020 ◽  
Vol 18 (24) ◽  
pp. 4519-4532 ◽  
Author(s):  
Hui Chen ◽  
Shouyun Yu
Keyword(s):  
Hydrogen Atom ◽  
Visible Light ◽  
Bond Formation ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer ◽  
Photoredox Catalysis ◽  
Recent Advances ◽  
Intramolecular Hydrogen

Visible light photoredox catalysis combined with intramolecular hydrogen atom transfer (HAT) can serve as a unique tool for achieving remote C–C bond formation. Recent advances in photoredox-catalyzed remote C–C bond formation are summarized.

Visible light photoredox-catalysed remote C–H functionalisation enabled by 1,5-hydrogen atom transfer (1,5-HAT)

2021 ◽  
Author(s):  
Weisi Guo ◽  
Qian Wang ◽  
Jieping Zhu
Keyword(s):  
Hydrogen Atom ◽  
Visible Light ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer

The generation of heteroatom-centred radicals followed by intramolecular 1,5-HAT and functionalisation of the translocated carbon-centred radical is an efficient way to functionalize chemo- and regio-selectively the remote unactivated C(sp3)–H bond.

Benzylic C–H heteroarylation of N-(benzyloxy)phthalimides with cyanopyridines enabled by photoredox 1,2-hydrogen atom transfer

2020 ◽  
Vol 56 (61) ◽  
pp. 8671-8674
Author(s):  
Long-Jin Zhong ◽  
Hong-Yu Wang ◽  
Xuan-Hui Ouyang ◽  
Jin-Heng Li ◽  
De-Lie An
Keyword(s):  
Hydrogen Atom ◽  
Visible Light ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer

Visible light initiated α-C(sp3)–H hetroarylation of N-(benzyloxy)phthalimides with cyanopyridines via 1,2-hydrogen atom transfer is depicted.

scholarly journals Photo-triggered hydrogen atom transfer from an iridium hydride complex to unactivated olefins

2020 ◽  
Vol 11 (32) ◽  
pp. 8582-8594
Author(s):  
Mirjam R. Schreier ◽  
Björn Pfund ◽  
Xingwei Guo ◽  
Oliver S. Wenger
Keyword(s):  
Hydrogen Atom ◽  
Visible Light ◽  
Electron Donor ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer ◽  
Hydride Complex ◽  
Proton Source

Upon irradiation with visible light, an iridium hydride complex undergoes hydrogen atom transfer (HAT) to unactivated olefins in presence of a sacrificial electron donor and a proton source.

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.

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