Radical Allylation, Vinylation, Allenylation, Alkynylation, and Propargylation Reactions Using Tin Reagents DOI

Ian J. Rosenstein

Organic reactions, Journal Year: 2022, Volume and Issue: unknown, P. 1 - 654

Published: June 13, 2022

This chapter describes the use of allyl‐ and vinylstannane reagents for a variety radical‐based transformations. The processes discussed include direct addition radicals to vinylstannanes, multicomponent or multistep cascade reactions that terminate with an intermolecular allylation vinylation, cyclizations onto moieties, allylstannylation reactions. Allylation have provided framework exploration stereoselective radical reactions, models explaining stereoselectivity obtained by number approaches are presented. Examples illustrate scope applications in synthesis, as well ways newly introduced allyl vinyl groups been subsequently manipulated. A comparison is made vinylation employ non‐tin‐based reagents.

Language: Английский

Visible-Light-Mediated Synthesis of Thio-Functionalized Pyrroles DOI
Ashish Kumar Sahoo, Amitava Rakshit, Anjali Dahiya

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(10), P. 1918 - 1923

Published: March 7, 2022

An inimitable illustration of the green-light-induced synthesis thio-functionalized pyrroles has been established using β-ketodinitriles and thiophenols as reacting partners eosin Y photocatalyst. Large-scale some useful synthetic modifications are also demonstrated.

Language: Английский

Citations

43

2H‐Azirines: Recent Progress in Synthesis and Applications DOI
Fen Xu,

Fan‐Wang Zeng,

Wenjie Luo

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(11)

Published: Jan. 29, 2024

Abstract 2H ‐arizines are important three‐membered heterocycles in organic chemistry. Recently, many advances the synthesis and functionalization of have been reported. Neber rearrangement, isomerization isoxazole, oxidation enamine, C−H bond activation, decomposition vinyl azide, alkyne, multi‐step developed for efficient assembly ‐azirines. As versatile highly strained unsaturated heterocycles, ‐azirines can be used as distinctive building blocks towards significant functional groups, attracted extensive attention fabrication numerous heterocycles. Recent studies focused on [3+n] ring‐expansion reactions, nucleophilic addition C=N double or continuous followed by cyclization, ring‐opening to acyclic compounds, substitution sp 3 ‐C−H One most critical challenges is seeking a selective opening specific three bonds azirine circle, some what achieved basis metal catalyst, photocatalysis, combination catalyst photocatalysis. In this review, recent involving reactivity accompanied with breakthroughs summarized. The review mainly covers period from 2019 2023.

Language: Английский

Citations

11

Palladium/Silver Cocatalyzed Divergent Dimerization of 2H-Azirines for Regioselective Synthesis of Tetrasubstituted Pyrroles and Pyrimidines DOI

Yongxing Zhao,

Rui Li,

Qingzheng Zhao

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(21), P. 3978 - 3983

Published: May 18, 2023

The unprecedented dimerizations of 2H-azirines have been developed under the catalysis palladium and silver. Upon changing reaction conditions, fully aryl-substituted pyrrole pyrimidine derivatives were furnished in moderate yields with regiospecificity, respectively. Control experiments uncovered distinct catalytic effects two transition metals, proposed cycles plausibly rationalized chemodivergence regioselectivity.

Language: Английский

Citations

11

Substituted 2H-azirine derivatives - Versatile reagents to access skeletal diversity DOI

Mahsa Farivar,

Reihane Peirow,

Aida Iraji

et al.

Journal of Molecular Structure, Journal Year: 2025, Volume and Issue: unknown, P. 142148 - 142148

Published: March 1, 2025

Language: Английский

Citations

0

Heterocycle Synthesis Through Photochemical Transformation of 2H-Azirines DOI
Bao‐Gui Cai, Jun Xuan

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

Published: Jan. 1, 2025

Language: Английский

Citations

0

Synthesis of Δ1-Pyrrolines via Formal (3 + 2)-Cycloaddition of 2H-Azirines with Enones Promoted by Visible Light under Continuous Flow DOI Creative Commons
Lorena S. R. Martelli, Lucas G. Furniel, Pedro H. O. Santiago

et al.

ACS Omega, Journal Year: 2025, Volume and Issue: unknown

Published: April 22, 2025

Language: Английский

Citations

0

Light-induced synthesis of 2H-azirines and its applications in organic chemistry DOI Creative Commons

Shibo Lin,

Yiwen Chu,

Junfeng Deng

et al.

Journal of Saudi Chemical Society, Journal Year: 2024, Volume and Issue: 28(2), P. 101831 - 101831

Published: March 1, 2024

2H-azirines have represented versatile building motifs in the domain of organic chemistry owing to their excellent reaction activity induced by high strain three-membered ring species. Over past decades, brilliant achievements been made 2H-azirine involving construction as well transformation such functional compounds. In presence transition metals, strong bases or oxidants, could be converted into corresponding products under harsh conditions. Different from traditional catalytic methods, utilization photochemistry has proved an extremely fascinating protocol that facilitates blocks diverse substrates and further conversion various derivatives with interesting biological activities. this regard, more light-driven synthetic approaches featuring efficiency mild conditions developed. Herein, we summarized accessibility applications powerful precursors key intermediates for synthesis biologically promising molecules photocatalytic

Language: Английский

Citations

3

Telescoped Flow Synthesis of Azacyclic Scaffolds Exploiting the Chromoselective Photolysis of Vinyl Azides and Azirines DOI Creative Commons
Ruairi Crawford, Marcus Baumann

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(38)

Published: May 8, 2024

An efficient chromoselective photochemical process is presented for the synthesis of 2H-azirines and 1,3-diazabicylo[3.1.0]hex-3-enes from readily available vinyl azides. The method exploits continuous flow photochemistry to enable safe consumption hazardous azide group provides uniform irradiation using high-power LEDs at 365-450 nm. Additionally, a scaled telescoped has been developed providing access drug-like 1,6-dihydropyrimidines pyrimidines via integrated ring-expansion oxidation reactions. Given prevalence various azacyclic targets in pharmaceutical, agrochemical materials applications it anticipated that this methodology will further exploitations these important scaffolds.

Language: Английский

Citations

3

Visible light-driven [3 + 3] annulation reaction of 2H-azirines with Huisgen zwitterions and synthesis of 1,2,4-triazines DOI
Shixuan Cao, Tong B. Tang, Jiatian Li

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(12), P. 3342 - 3347

Published: Jan. 1, 2022

A visible light-driven [3 + 3] annulation reaction of 2 H -azirines with Huisgen zwitterions is developed for the first time.

Language: Английский

Citations

13

Visible‐Light‐Promoted [3 + 2] Cycloaddition of 2H‐Azirines with Quinones: Access to Substituted Benzo[f]isoindole‐4,9‐diones DOI
Lijia Wang, Chuang Liu, Lei Li

et al.

Chinese Journal of Chemistry, Journal Year: 2021, Volume and Issue: 40(6), P. 719 - 724

Published: Nov. 24, 2021

Comprehensive Summary A visible‐light‐promoteded [3 + 2] cycloaddition reaction of 2 H ‐azirines with quinones has been developed under mild conditions. The provides a general and efficient strategy for the synthesis benzo[ f ]isoindole‐4,9‐diones scaffold via tandem cyclization/oxidative aromatization molecular oxygen. Furthermore, preliminary studies photocatalytic properties show that 3 can be used as photocatalysts in several organic transformations.

Language: Английский

Citations

17