Direct Synthesis of α‐Aryl‐α‐Trifluoromethyl Alcohols via Nickel Catalyzed Cross‐Electrophile Coupling DOI Creative Commons
Lorenzo Lombardi,

Alessandro Cerveri,

Riccardo Giovanelli

et al.

Angewandte Chemie, Journal Year: 2022, Volume and Issue: 134(47)

Published: Sept. 26, 2022

Abstract A nickel‐catalyzed reductive cross‐electrophile coupling between the redox‐active N‐ trifluoroethoxyphthalimide and iodoarenes is documented. The protocol reproduces a formal arylation of trifluoroacetaldehyde under mild conditions in high yields (up to 88 %) with large functional group tolerance (30 examples). combined computational experimental investigation revealed pivotal solvent assisted 1,2‐Hydrogen Atom Transfer (HAT) process generate nucleophilic α‐hydroxy‐α‐trifluoromethyl C‐centered radical for Csp 2 −Csp 3 bond forming process.

Language: Английский

The literature of heterocyclic chemistry, part XXII, 2022 DOI
Галина А. Газиева, Yu. B. Evdokimenkova, N. O. Soboleva

et al.

Advances in heterocyclic chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

Citations

0

Ni‐Catalyzed Cross‐Electrophile Couplings of N‐Alkoxyphthalimides and Aryl Halides DOI Creative Commons

John J. Monteith,

Sophie A. L. Rousseaux

European Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 13, 2025

N ‐alkoxyphthalimides represent a versatile class of redox‐active alcohol derivatives for carbon–carbon bond formation following activation by single‐electron reduction. Herein, key precedents using the new bonds under photochemical reaction conditions are first presented. The merger these and other strategies with Ni catalysis in various cross‐electrophile couplings aryl halides is then highlighted. A particular focus made on mechanisms proposed Ni‐catalyzed reductive cross‐couplings. Concluding thoughts future design as C(sp 3 )O transition metal‐catalyzed cross‐couplings also

Language: Английский

Citations

0

N-Alkoxyphthalimides as Nitrogen Electrophiles to Construct C–N Bonds via Reductive Cross-Coupling DOI
Kang Wu,

Tian‐Zhang Wang,

Chao‐Peng Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10004 - 10011

Published: June 27, 2024

-Alkoxyphthalimides, one kind of phthalimide derivative, have great importance in synthesis, mainly used as free radical precursors. While the unit, for a long time, was treated part waste stream. Construction C-N bonds has always been hot spot, especially reductive cross-coupling. Herein, nickel-catalyzed cross-coupling reaction

Language: Английский

Citations

2

Photoredox-catalyzed, oxygen-directed unactivated δ-C(sp3)–H functionalization toward oxepanes DOI

Hao Wu,

Shi-Hui He,

Haitao Qin

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(15), P. 3870 - 3874

Published: Jan. 1, 2023

A concise photoredox-catalyzed [5 + 2] annulation reaction is developed for the synthesis of alkene/alkyne-containing oxepanes.

Language: Английский

Citations

5

Silver-catalyzed cyclization of α-imino-oxy acids to fused tetralone derivatives DOI
Kai Liu, Feng Li, Jingjing Wang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(13), P. 2700 - 2704

Published: Jan. 1, 2023

A silver-catalyzed cyclization of α-imino-oxy acids under mild conditions has been described. This reaction offers facile access to a diverse range fused tetralone derivatives with exquisite stereoselectivity in moderate good yields.

Language: Английский

Citations

4

Visible-Light-Driven α-C(sp3)–H Bond Functionalization of Glycine Derivatives DOI Open Access

Yao Tian,

Xiubin Bu,

Yuanrui Chen

et al.

Catalysts, Journal Year: 2023, Volume and Issue: 13(12), P. 1502 - 1502

Published: Dec. 8, 2023

The glycine motif is widely prevalent in bioactive peptides. Thus, the direct and precise modification of derivatives has attracted significant attention over past few decades. Among various protocols for derivatives, visible-light-driven α-C(sp3)–H bond functionalization emerged as a powerful tool to achieve this objective, owing its merits atom economy, selectivity, reaction simplicity, sustainability. This review summarizes recent advancements derivatives. contents are organized based on photocatalysts employed modes process. mechanism, challenges encountered, future trends also discussed, enabling readers understand current developmental status field.

Language: Английский

Citations

4

Photochemical Decarboxylative Radical Alkylation/Cyclization Reaction to Fused Nitrogen Heterocycles by LiI/PPh3 Catalysis DOI

Jia‐Li Sui,

Xin‐Qian Liu,

Shun‐Dan Li

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 10, 2024

Comprehensive Summary A visible‐light‐induced decarboxylative radical cascade cyclization reaction between N ‐(2‐cyanoaryl)‐acrylamides and alkyl ‐(acyloxy)phthalimide (NHPI esters) for the construction of phenanthridine derivatives has been developed. This approach utilizes lithium iodide (LiI) triphenylphosphine (PPh 3 ) as redox catalysts is produced through photoactivation electron donor‐acceptor (EDA) complex. series primary, secondary, tertiary alkyl‐substituted phenanthridines are prepared in up to 82% yield without transition‐metal catalysts, chemical oxidants, or metal‐/organic dye‐based photocatalysts.

Language: Английский

Citations

1

Recent Uses of Photogenerated Oxygen-Centered Radicals in Intermolecular C–O Bond Formation DOI
Guillaume Dagousset,

Camille Banoun,

Emmanuel Magnier

et al.

Synlett, Journal Year: 2023, Volume and Issue: 35(03), P. 268 - 278

Published: July 18, 2023

Abstract We report herein recent advances made by our group and others in the field of oxygen-centered radicals generated under photocatalysis. Thanks to design new O-radical precursors, these can now be efficiently trapped unsaturated systems an intermolecular manner, via formation a C–O bond. 1 Introduction 2 Reactions Involving Carbonyloxy Radicals 3 Fluoroalkoxy 4 Alkoxy 5 Conclusion

Language: Английский

Citations

2

Highly efficient electrogeneration of oxygen centered radicals from N-alkoxyphthalimides employing rapid alternating polarity (RAP) electrolysis. Transferring the photoredox catalytic conditions to organic electrosynthesis DOI Creative Commons
Julio Romero‐Ibañez, Diego Francisco Chicas‐Baños, Fernando Sartillo‐Piscil

et al.

Current Research in Green and Sustainable Chemistry, Journal Year: 2024, Volume and Issue: 8, P. 100404 - 100404

Published: Jan. 1, 2024

The first electrogeneration of O-centered radicals from N-alkoxyphthalimides via rapid alternating polarity (RAP) electrolysis, using previous experimental conditions photoredox catalysis (PRC) is reported. electrochemical methodology emulates satisfactorily the redox cycle behavior accepted to explain PRC technique. Notably, contribution oxidized Hantzsch ester produced during anodic reaction emphasized, which behaves as an efficient proton donor facilitate N–O cleavage and extinguish radical sequence efficiently. conducted in a practical way undivided cell fitted with glassy carbon electrodes, allowing same reactions occur on both electrodes overall transformation reaching 77% yield corresponding alcohol. This higher than protocol direct current confirming that use RAP electrolysis favors proximity where reactive intermediates are produced, facilitating their promote desired pathway.

Language: Английский

Citations

0

3-Halo-5,6-dihydro-4H-1,2-oxazine N-oxides as synthetic equivalents of unsaturated nitrile oxides in the [3 + 2]-cycloaddition with arynes: synthesis of substituted 3-vinyl-1,2-benzisoxazoles DOI
Alexander A. Lukoyanov, Svetlana A. Aksenova, Andrey A. Tabolin

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(18), P. 3615 - 3621

Published: Jan. 1, 2024

The reaction of 3-halo-5,6-dihydro-4

Language: Английский

Citations

0