Photochemical Synthesis and Ring‐Opening of Aziridines and Epoxides: State‐of‐the‐Art DOI
Lucas G. Furniel, Arlene G. Corrêa

ChemPhotoChem, Journal Year: 2024, Volume and Issue: 8(9)

Published: May 13, 2024

Abstract The development of greener methods for the preparation three‐membered rings has increased in last decade, not only due to their biological activity but also ring strain those heterocycles that make them useful precursors more complex molecules. In this work, visible‐light‐promoted synthesis and ring‐opening aziridines epoxides, reported five years, were reviewed. Both homogeneous heterogeneous catalysts discussed and, addition, plausible mechanism pathways highlighted.

Language: Английский

Skeletal Editing by Hypervalent Iodine Mediated Nitrogen Insertion DOI
Srimanta Manna, Joydev K. Laha, Anjali Gupta

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: July 24, 2024

Hypervalent iodine reagents are versatile and readily accessible that have been extensively applied in contemporary synthesis modern organic chemistry. Among them, iodonitrene (ArI=NR), is a powerful reactive species, widely used for single-nitrogen-atom insertion reaction, skeletal editing to construct N-heterocycles. Skeletal with components has recently emerged as an exciting approach chemical transformation. These produce biologically relevant heterocycles functionalized molecular architectures. Recently, the of nitrogen-atom into hydrocarbons generate N-heterocyclic compounds using hypervalent significant focus field reactions. In this review, we discuss rapidly emerging nitrene insertion, including nitrogen access nitrogen-containing heterocycles, current mechanistic understanding these processes.

Language: Английский

Citations

5
Photocatalytic Nitrene Radical Anion Generation from Sulfonyl Azides for Intermolecular Aziridination of Unactivated Alkenes DOI Creative Commons
Dennis Dam,

Joeri Schoenmakers,

Elisabeth Bouwman

et al.

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

Published: May 3, 2025

Aziridines are important structures in the contemporary organic synthesis and used for several biological applications. Herein, we show that aziridines can be readily synthesized from alkenes by reductive activation of sulfonyl azides, mediated photoredox catalysis. Mechanistic studies indicate reaction proceeds through reactive nitrene radical anions instead more commonly encountered triplet nitrenes. A substrate scope is performed showed good functional group compatibility.

Language: Английский

Citations

0
The efficient synthesis of three-membered rings via photo- and electrochemical strategies DOI Creative Commons
Xinyu Han, Na Zhang, Qiannan Li

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(34), P. 13576 - 13604

Published: Jan. 1, 2024

Three-membered rings, such as epoxides, aziridines, oxaziridines, cyclopropenes, vinyloxaziridines, and azirines, are recognized crucial pharmacophores building blocks in organic chemistry drug discovery. Despite the significant advances synthesis of these rings through photo/electrochemical methods over past decade, there has currently been no focused discussion updated overviews on this topic. Therefore, we presented review article efficient three-membered using photo- electrochemical strategies, covering literature since 2015. In study, a conceptual overview detailed discussions were provided to illustrate advancement field. Moreover, brief outlines current challenges opportunities synthesizing strategies.

Language: Английский

Citations

2
Copper(I)‐Photocatalyzed Diastereoselective Aziridination of N‐Sulfonyl Imines with Vinyl Azides: Application to Benzo[f][1,2,3]oxathiazepines Dioxides and Fused Isoxazolines DOI

S Banuprakash Goud,

Raju Lal Dhakar,

Sampak Samanta

et al.

Chemistry - An Asian Journal, Journal Year: 2023, Volume and Issue: 19(2)

Published: Nov. 29, 2023

Abstract An in situ generated photoactive copper(I)‐complex‐catalyzed aziridination reaction of cyclic N‐sulfonyl imines with α‐aryl‐substituted vinyl azides irradiated by blue‐LEDs light is reported for the first time. This novel SET process represents a mild, sustainable, and pragmatic method accessing synthetically resourceful sulfamidate‐fused aziridines acceptable chemical yields excellent diastereoselectivities. Delightedly, pharmacologically attractive benzo[ f ][1,2,3]oxathiazepine dioxides fused isoxazoline frameworks were achieved through our newly developed metal‐free based ring‐expansion techniques, highlighting synthetic value accessed aziridines. Finally, possible mechanism [2+1] aza‐cyclization was presented on conduction series control experiments.

Language: Английский

Citations

4
Photochemical Synthesis and Ring‐Opening of Aziridines and Epoxides: State‐of‐the‐Art DOI
Lucas G. Furniel, Arlene G. Corrêa

ChemPhotoChem, Journal Year: 2024, Volume and Issue: 8(9)

Published: May 13, 2024

Abstract The development of greener methods for the preparation three‐membered rings has increased in last decade, not only due to their biological activity but also ring strain those heterocycles that make them useful precursors more complex molecules. In this work, visible‐light‐promoted synthesis and ring‐opening aziridines epoxides, reported five years, were reviewed. Both homogeneous heterogeneous catalysts discussed and, addition, plausible mechanism pathways highlighted.

Language: Английский

Citations

1