scholarly journals C(sp3)–H Bond Acylation with N-Acyl Imides under Photoredox/ Nickel Dual Catalysis

Synlett ◽  
2020 ◽  
Author(s):  
Abderrahmane Amgoune ◽  
Taline Kerackian ◽  
Antonio Reina ◽  
Tetiana Krachko ◽  
Hugo Boddaert ◽  
...  
Keyword(s):  
Hydrogen Atom ◽  
Bond Activation ◽  
Hydrogen Atom Transfer ◽  
Acyl Transfer ◽  
Atom Transfer ◽  
Mild Conditions ◽  
Dual Catalysis ◽  
Dialkyl Ethers

AbstractA novel Ni/photoredox-catalyzed acylation of aliphatic substrates, including simple alkanes and dialkyl ethers, has been developed. The method combines C–N bond activation of amides with a radical relay mechanism involving hydrogen-atom transfer. The protocol is operationally simple, employs bench-stable N-acyl imides as acyl-transfer reagents, and permits facile access to alkyl ketones under very mild conditions.

scholarly journals Synthesis of Spirocyclic Piperidines by Radical Hydroarylation

Synlett ◽  
2020 ◽  
Author(s):  
Racheal M. Spurlin ◽  
Amber L. Harris ◽  
Nathan T. Jui ◽  
Cameron J. Pratt
Keyword(s):  
Hydrogen Atom ◽  
Aryl Halide ◽  
Precious Metals ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer ◽  
Aryl Radical ◽  
Radical Species ◽  
Mild Conditions

AbstractReported here are conditions for the construction of spirocyclic piperidines from linear aryl halide precursors. These conditions employ a strongly reducing organic photoredox catalyst in combination with a trialkylamine reductant to achieve formation of aryl radical species. Regioselective cyclization followed by hydrogen-atom transfer affords a range of complex spiropiperidines. This system operates efficiently under mild conditions without the need for toxic reagents or precious metals.

scholarly journals Titanium and Cobalt Bimetallic Radical Redox Relay for the Isomerization of N-Bz Aziridines to Allylic Amides

Synthesis ◽  
2021 ◽  
Author(s):  
Song Lin ◽  
Devin P. Wood ◽  
Weiyang Guan
Keyword(s):  
Hydrogen Atom ◽  
Hydrogen Atom Transfer ◽  
Alternative Strategy ◽  
Atom Transfer ◽  
Allylic Amination ◽  
Alkyl Radicals ◽  
Mild Conditions

AbstractHerein a bimetallic radical redox-relay strategy is employed to generate alkyl radicals under mild conditions with titanium(III) catalysis and terminated via hydrogen atom transfer with cobalt(II) catalysis to enact base-free isomerizations of N-Bz aziridines to N-Bz allylic amides. This reaction provides an alternative strategy for the synthesis of allylic amides from alkenes via a three-step sequence to accomplish a formal transpositional allylic amination.

Mechanistic insights into the reactions of hydride transfer versus hydrogen atom transfer by a trans-dioxoruthenium(vi) complex

2015 ◽  
Vol 44 (16) ◽  
pp. 7634-7642 ◽  
Author(s):  
Sunder N. Dhuri ◽  
Yong-Min Lee ◽  
Mi Sook Seo ◽  
Jaeheung Cho ◽  
Dattaprasad D. Narulkar ◽  
...  
Keyword(s):  
Hydrogen Atom ◽  
Bond Activation ◽  
Hydride Transfer ◽  
Hydrogen Atom Transfer ◽  
Transfer Mechanism ◽  
Atom Transfer ◽  
High Valent

Valuable insights into the hydride-transfer mechanism and C–H bond activation reactions by high-valent trans-dioxoruthenium(vi) species is provided.

Recent Advances in Copper-Catalyzed Radical C–H Bond Activation Using N–F Reagents

Synthesis ◽  
2020 ◽  
Vol 53 (01) ◽  
pp. 51-64
Author(s):  
José María Muñoz-Molina ◽  
Tomás R. Belderrain ◽  
Pedro J. Pérez
Keyword(s):  
Hydrogen Atom ◽  
Bond Activation ◽  
Short Review ◽  
Industrial Applications ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer ◽  
Bond Functionalization ◽  
The Future ◽  
Intramolecular Hydrogen ◽  
Potential Use

This Short Review is aimed at giving an update in the area of copper-catalyzed C–H functionalization involving nitrogen-centered radicals generated from substrates containing N–F bonds. These processes include intermolecular Csp3–H bond functionalization, remote Csp3–H bond functionalization via intramolecular hydrogen atom transfer (HAT), and Csp2–H bond functionalization, which might be of potential use in industrial applications in the future.1 Introduction2 Intermolecular Csp3–H Functionalization3 Remote Csp3–H Functionalization4 Csp2–H Functionalization5 Conclusion

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