Electrochemical selenium-catalyzed para-amination of N-aryloxyamides: access to polysubstituted aminophenols DOI
Lei Gao, Zhifeng Wang,

Lin‐Wei Wang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(39), P. 7895 - 7899

Published: Jan. 1, 2023

Aminophenols are a class of important compounds with various pharmacological activities such as anticancer, anti-inflammatory, antimalarial, and antibacterial activities. Herein, we introduce mild efficient electrochemical selenium-catalyzed strategy to synthesize polysubstituted aminophenols. High atom efficiency transition metal-free oxidant-free conditions the striking features this protocol. By merging organoselenium-catalyzed processes, intramolecular rearrangement N-aryloxyamides produces para-amination products at room temperature in simple undivided cell.

Language: Английский

Transition Metal and Base‐Free Electro‐Oxidative Regioselective Trifluoromethylation of Imidazo[1,2‐a]pyridines DOI
Atreyee Halder, Sayan Ghosh, Suman De Sarkar

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(8)

Published: June 27, 2023

Abstract A green electrochemical C(sp 2 )−H trifluoromethylation of imidazo[1,2‐ a ]pyridines by engaging Langlois’ reagent is reported. This oxidative regioselective CF 3 ‐functionalization strategy operates under open atmosphere, in an undivided cell and at ambient temperature. Regioselective C−CF bond formation was achieved exclusively applying this mild protocol exhibiting broad functional group compatibility affording the desired product up to 79% isolated yield. Mechanistic studies indicated radical pathway for redox transformation.

Language: Английский

Citations

6

Electro-oxidative Synthesis of Unsymmetrical Alkyne-1,4-diones via Sequential Ring Formation and Cleavage DOI
Atreyee Halder, Debabrata Maiti,

Jhilik Dutta

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(41), P. 7578 - 7583

Published: Oct. 9, 2023

Synthesis of unsymmetrical but-2-yne-1,4-diones is reported through oxidative alkyne translocation readily accessible homopropargylic alcohols. The developed method consists an unprecedented one-pot sequential electro-oxidative annulation-fragmentation-chemical selenoxide elimination process. Excellent functional group compatibility was observed, and array yne-1,4-diones were synthesized. Derivatization the gave access to other valuable scaffolds. Detailed mechanistic studies isolation key intermediates clarified cascade transformation.

Language: Английский

Citations

6

Transition-Metal-Free Electrochemical Selenylative Cyclization of Alkynyl Phosphonates DOI
Bo Li, Yunhao Zhou, Yue Xu

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(21), P. 15414 - 15427

Published: Oct. 23, 2023

Unprecedented regioselective electrochemical tandem selenation/cyclization of alkynyl phosphonates with diselenide is described here. These obtained selenoether products can be chemo-selectively converted into halogen-functionalized cyclic enol under our conditions. protocols provide straightforward access to valuable phosphonate or phosphaisocoumarins the and transition-metal-free The robustness these transformations was illustrated by their compatibility various complex natural bioactive molecules. halogen functional groups allow further diversification phosphorus heterocycles thus obtained.

Language: Английский

Citations

6

Organoselenium Compounds in Catalysis DOI
Juan B. Rodríguez, Carola Gallo‐Rodriguez

Synthesis, Journal Year: 2023, Volume and Issue: 56(15), P. 2295 - 2315

Published: Oct. 24, 2023

Abstract In this article we have focused on the use of selenium in catalysis along with proposed reaction mechanisms. With increasing interest chemistry, highlighted most significant features subject, mainly last years. Selenium-containing catalysts a key role many transformations; for example, oxidation reactions that are performed under very mild and controlled conditions. addition, utilizing weak selenium–oxygen bonding interaction has proved to be useful as catalytic approach specific transformations. The cycles each appropriate transformation fully reviewed. 1 Introduction 2 Use Selenium Catalysis: Perspectives 2.1 Directing Group: Preparation Organoselenium Compounds via C–H Borylation 2.2 Multicomponent Reactions Employing Catalyst 2.3 Selenium-π-Acid Catalysts 2.4 Electrochemical Selenium-Catalyzed 2.5 Stereoselective Synthesis 2.6 Transition-Metal Containing Selenium-Based Ligands 2.6.1 Selenium-Ligated Palladium(II) Complexes Heck Reaction 2.6.2 Pincer Allylation Aldehydes Closely Related Functional Groups 2.6.3 Employed Buchwald-Type C–N Coupling 2.6.4 Suzuki–Miyaura 2.7 Catalysis Michael-Type 2.8 Catalytic Cycle Glutathione Peroxidase 2.9 Epoxidation 2.10 Dihydroxylation 2.11 Oxidation 2.12 Bromolactonization 2.13 Alkenes from Vicinal Diols 2.14 α-Selanyl Enals Propargylic Alcohols 2.15 Miscellanea 3 Concluding Remarks

Language: Английский

Citations

6

Electrochemical Synthesis of 4‐Selenylated Oxazolones via Oxyselenylation of Ynamides DOI Open Access
Jinhui Cai,

Kaili Cen,

Weishuang Li

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 19, 2024

Abstract Electrosynthesis of selenylated‐oxazolone derivatives via cascade selenylation/cyclization ynamides was disclosed. A series diaryl diselenides, dialkyl and heteroaryl‐substituted tolerated in this protocol delivered 4‐selenyloxazolones 28–83% yields. The scale‐up reaction the oxidation performed to showcase practicability method. Furthermore, mechanistic experiments indicated that a cationic pathway instead radical probably involved.

Language: Английский

Citations

2

Photo-induced organoselenium-catalyzed synthesis of 2-substituted quinazoline derivatives DOI
Hong Yang, Wenli Li, Yihong Wang

et al.

Journal of Molecular Structure, Journal Year: 2023, Volume and Issue: 1297, P. 136940 - 136940

Published: Oct. 27, 2023

Language: Английский

Citations

5

Efficient C(sp3)−H Carbonylation of Light and Heavy Hydrocarbons with Carbon Monoxide via Hydrogen Atom Transfer Photocatalysis in Flow** DOI Creative Commons
Fabian Raymenants, Tom M. Masson, J. Orduna

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(36)

Published: July 17, 2023

Abstract Despite their abundance in organic molecules, considerable limitations still exist synthetic methods that target the direct C−H functionalization at sp 3 ‐hybridized carbon atoms. This is even more case for light alkanes, which bear some of strongest bonds known Nature, requiring extreme activation conditions are not tolerant to most molecules. To bypass these issues, chemists rely on prefunctionalized alkyl halides or organometallic coupling partners. However, new regioselectively a variety different scaffolds would be great added value, only late‐stage biologically active molecules but also catalytic upgrading cheap and abundant hydrocarbon feedstocks. Here, we describe general, mild scalable protocol enables C(sp )−H carbonylation saturated hydrocarbons, including natural products using photocatalytic hydrogen atom transfer (HAT) gaseous monoxide (CO). Flow technology was deemed crucial enable high gas‐liquid mass rates fast reaction kinetics, needed outpace deleterious pathways, leverage safe process.

Language: Английский

Citations

4

Recent Advances in Electrochemically Mediated Reactions of Diselenides DOI Creative Commons
Zu‐Yu Mo, Ying‐Ming Pan,

Lei Zhan

et al.

SynOpen, Journal Year: 2023, Volume and Issue: 07(04), P. 521 - 534

Published: Sept. 6, 2023

Abstract Organoselenium compounds are crucial molecules that utilized extensively in diverse fields such as medicine, agriculture, catalysis, and organic materials. The incorporation of selenium atoms into holds significant importance synthetic chemistry. Organic electrochemical synthesis, a green, mild, efficient strategy, has displayed remarkable potential for organoselenium chemistry synthesis. Consequently, there been substantial interest recent years researching electrochemically mediated synthesis compounds. This review provides an overview the progress made reactions over last decade, including oxidation diselenide coupling, tandem selenocyclization. scope, limitations, mechanisms those emphasized. 1 Introduction 2 Electrochemical Selenium-Catalyzed Reactions 3 Electrochemically Mediated Coupling Aromatic/Heterocyclic Rings with Diselenides 4 Tandem Selenocyclization 5 Conclusion

Language: Английский

Citations

4

Electrochemical N-olefination for the regio- and stereo-selective synthesis of vinyl azoles DOI Creative Commons
Kejun Lin,

Jianyong Lan,

Hao Lin

et al.

Green Synthesis and Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

A selenium-catalyzed electrosynthesis involving regio- and stereo-selective N-olefination of azoles was developed. The room-temperature reaction efficient (up to 97% yield) compatible with various styrenes azoles. Mechanistic study showed that the cascade triggered by selenium-cation-mediated electrophilic trans-aminoselenation, followed an oxidative cis-elimination selane. also well more challenging internal alkene substrates, giving desired N-vinyl in up 88% yield > 20:1 Z/E ratio.

Language: Английский

Citations

0

Electrochemical selenium-catalyzed para-amination of N-aryloxyamides: access to polysubstituted aminophenols DOI
Lei Gao, Zhifeng Wang,

Lin‐Wei Wang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(39), P. 7895 - 7899

Published: Jan. 1, 2023

Aminophenols are a class of important compounds with various pharmacological activities such as anticancer, anti-inflammatory, antimalarial, and antibacterial activities. Herein, we introduce mild efficient electrochemical selenium-catalyzed strategy to synthesize polysubstituted aminophenols. High atom efficiency transition metal-free oxidant-free conditions the striking features this protocol. By merging organoselenium-catalyzed processes, intramolecular rearrangement N-aryloxyamides produces para-amination products at room temperature in simple undivided cell.

Language: Английский

Citations

0