Electrochemical Synthesis of Phosphorylated Azaspiro[4.5]di/trienones through Dearomative Spirocyclization DOI

Xiaocong Zhou,

Jian Wang, Dumei Ma

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(57), P. 7351 - 7354

Published: Jan. 1, 2024

Cp 2 Fe-mediated electrochemical synthesis of a diverse array phosphorylated azaspiro[4.5]di/trienones has been developed, which demonstrated broad substrate scope and good diastereoselectivity.

Language: Английский

Electrochemical Dearomative Spirocyclization DOI
Nan Li, Zhaojiang Shi,

Wei‐Zhen Wang

et al.

Chemistry - An Asian Journal, Journal Year: 2023, Volume and Issue: 18(9)

Published: March 15, 2023

Electrochemical dearomative spirocyclization serves as a green and sustainable approach to convert the flat, two-dimension aromatic feedstock into value-added three-dimension spirocyclic architectures. This review highlights recent advances, emphasizes mechanistic discussions, showcases synthetic applications of this emerging versatile powerful transformation.

Language: Английский

Citations

36

Electrochemical cascade migratory versus ortho-cyclization of 2-alkynylbenzenesulfonamides DOI Creative Commons
Zhaojiang Shi, Shicheng Dong, Ting Liu

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(8), P. 2827 - 2832

Published: Jan. 1, 2024

Efficient control over several possible reaction pathways of free radicals is the chemical basis their highly selective transformations. Among various competing pathways, sulfonimidyl generated from electrolysis 2-alkynylbenzenesulfonamides undergo cascade migratory or

Language: Английский

Citations

7

Electrochemical synthesis of selenyl imidazo[2,1-b]thiazinones via three-component reactions DOI

Yuancheng Yue,

Ziren Chen, Fei Xue

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(20), P. 5813 - 5819

Published: Jan. 1, 2024

In this paper, we have developed an efficient strategy for the concise synthesis of diverse selenyl imidazo[2,1- b ]thiazinones via electrochemical oxidative three-component tandem reactions in absence transition metals, and oxidants.

Language: Английский

Citations

4

Research Advances in Electrochemical Synthesis of Spirocyclic Skeleton Compounds DOI
Mu‐Xue He, Ying‐Ming Pan, Qian Wang

et al.

Synthesis, Journal Year: 2023, Volume and Issue: 55(18), P. 2873 - 2895

Published: Jan. 24, 2023

Abstract Spirocyclic compounds have attracted the interest of synthetic chemists because their unique ring systems and utility in drug discovery. Many natural containing spirocyclic moieties skeleton are effective pharmaceuticals. For many redox processes, electroorganic synthesis is considered an environmentally friendly method, since use reagents with significant toxicity replaced by electric current, so amount waste often greatly reduced. Therefore, this review summarizes construction a via electrochemical strategies 2000. 1 Introduction 2 Electrochemically Mediated Synthesis Spirocyclopropanes 3 Spirooxindoles 4 Spirodienones 5 Other Heterospirocycles 6 Conclusion

Language: Английский

Citations

10

Electrochemical Post-Ugi Cyclization for the Synthesis of Highly Functionalized Spirolactams DOI

Riya Nagar,

Dinesh Suwalka,

Bhanwar Kumar Malviya

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(19), P. 13977 - 13994

Published: Sept. 11, 2023

The combination of the Ugi reaction and electro-organic synthesis can aid in creation novel heterocycles that have not been previously explored. In this study, a new strategy utilizing bis-amides from has developed, which produce C–S, C–Se, C–C═O functionalized five-membered spirolactams mediated by electricity under catalyst- metal-free conditions. Notably, approach be applied using microelectro-flow reactor (μ-EFR) for gram-scale synthesis. described synthesize complex azaspiro-fused tricyclic scaffolds with high diastereo- regioselectivity, highlighting its versatility potential.

Language: Английский

Citations

10

Electrochemical Oxidative Dearomatization Strategy for Accessing Spiro[4.5]dienones and Derivatives DOI

Rohan Bag,

Nilima Priyadarsini Mishra, Debarshi Saha

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(4), P. 2200 - 2211

Published: Feb. 8, 2024

Electrochemical dearomatization has been recognized as an attractive tool for the rapid construction of structurally diverse molecules. The designed methodology encompasses eco-friendly and efficient electrochemical approach to synthesizing spiro[4.5]dienones under mild reaction conditions. Furthermore, detailed mechanistic studies strongly bolster our hypothesis emphasize role HFIP in mechanism. protocol is scalable showcases a broad substrate scope with tolerance toward numerous functional groups. Henceforth, this strategy can be deployed alternative sustainable accessing spiro[4.5]dienones.

Language: Английский

Citations

3

Electrochemical Continuous-Flow Scholl Reaction toward Polycyclic Aromatic Hydrocarbons DOI
Weizhen Wang, Qiang Wang,

Xinglei He

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(11), P. 2243 - 2248

Published: March 8, 2024

The preparation of polycyclic aromatic hydrocarbons (PAHs) by the Scholl reaction is typically performed using superstoichiometric oxidants. Herein, we develop an electrochemical continuous-flow to access PAHs that features a reduction in use supporting electrolytes and easy scale-up without changing conditions setups. This allows synthesis distorted containing three [5]helicene units possess intriguing electronic optical properties.

Language: Английский

Citations

3

Electrochemical Dearomative Amination of Phenol Derivatives: Access to Spirooxazolidinones DOI

Jin‐Lin Wan,

Jing‐Mei Huang

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(8), P. 1211 - 1216

Published: March 23, 2023

Abstract An electrochemical oxidative approach to spirooxazolidinones from phenol derivatives via intramolecular dearomative amination reactions is developed. This reaction proceeds without metal catalysts and external chemical oxidants, shows broad substrate scope diverse functional group compatibility. The synthetic utility of this strategy further exhibited by the gram‐scale synthesis late‐stage functionalization. By slightly tunning conditions, alcohols (1°, 2° 3°) can be afforded derivatives, which a good for deprotection para ‐methoxyphenyl (PMP) recover alcohol function. magnified image

Language: Английский

Citations

5

Electrochemical Dearomative Spirocyclization of N‐Acyl Sulfonamides in a Continuous‐Flow Cell DOI
Ting Liu, Zhaojiang Shi, Yaofeng Yuan

et al.

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 42(9), P. 980 - 984

Published: Dec. 26, 2023

Comprehensive Summary The development of efficient and sustainable methods to obtain spirocyclic compounds is significance as these structures are widely found in pharmaceuticals agrochemicals. Herein, we disclose an electrochemical dearomative spirocyclization N ‐acyl sulfonamides a continuous‐flow cell. reaction simple without external catalysts or supporting electrolytes could be applied decagram‐scale synthesis.

Language: Английский

Citations

5

Construction of N-Heterocycles via Electrochemically Generated Nitrogen Radicals and Nitrilium Ions DOI
Zhaojiang Shi, Ke‐Yin Ye

Topics in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Language: Английский

Citations

1