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.

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

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 C(sp3)-H alkenylation promoted by uranyl cation as a visible-light photocatalyst

2021 ◽  
Vol 2079 (1) ◽  
pp. 012020
Author(s):  
Zhiyu Feng
Keyword(s):  
Hydrogen Atom ◽  
Visible Light ◽  
Bond Formation ◽  
Cyclic Ether ◽  
Hydrogen Atom Transfer ◽  
Cyclic Ethers ◽  
Atom Transfer ◽  
Target Product ◽  
Visible Light Photocatalyst ◽  
Uranyl Cation

Abstract The alkenylation of cyclic ethers with β-nitroalkenes using uranyl cation as a photocatalyst is reported. Previous studies revealed the feasibility of incorporating organic photocatalyst in the visible light mediated alkenylation, while the uranyl cation serves as an alternative photocatalyst candidate successfully accomplish this transformation through a different pathway. The reaction features the direct hydrogen atom transfer (HAT) process to activate alpha C(sp3)-H of cyclic ether, and consequently cyclic ether is coupled with β-nitroalkene to give the target product with F-selectivity through C-C bond formation.

1.13 Intramolecular Hydrogen-Atom Transfer

2021 ◽  
Author(s):  
S. Treacy ◽  
X. Zhang ◽  
T. Rovis
Keyword(s):  
Hydrogen Atom ◽  
Functional Groups ◽  
Open Shell ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer ◽  
Stable Carbon ◽  
Radical Reactivity ◽  
Recent Advances ◽  
Synthetic Chemist ◽  
Intramolecular Hydrogen

AbstractRecent advances in intramolecular hydrogen-atom transfer (HAT) have demonstrated significant utility in C—H functionalization through highly reactive open-shell intermediates. The intramolecular transposition of radical reactivity from select functional groups to generate more stable carbon-centered radicals often proceeds with high regioselectivity, providing novel bond disconnections at otherwise inert and largely indistinguishable positions. This chapter explores the functional groups capable of intramolecular HAT to generate remote radicals and the transformations currently available to the synthetic chemist.

scholarly journals C-C Bond Formation by Sequential Intramolecular Hydrogen Atom Transfer/Intermolecular Radical Allylation Reaction in Carbohydrate Systems

2012 ◽  
Vol 2012 (20) ◽  
pp. 3818-3829 ◽  
Author(s):  
Elisa I. León ◽  
Ángeles Martín ◽  
Inés Pérez-Martín ◽  
Luís M. Quintanal ◽  
Ernesto Suárez
Keyword(s):  
Hydrogen Atom ◽  
Bond Formation ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer ◽  
Intramolecular Hydrogen

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.

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