Synthesis of cyclic silyl enol ethers from α-Aryl-α-diazoketones: new building blocks for preparation of indanones and α,β-unsaturated ketones DOI
Yueqiang Liu, Sheng Zhang, Yang Li

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(24), P. 6117 - 6123

Published: Jan. 1, 2023

A new strategy for in situ generation of vinyl cation intermediates from α-diazocarbonyl compounds is described this paper.

Language: Английский

Stabilizing Influence of Electron-Deficient Triazole Fragment on the Furan Heterocycle in Renewable Platform Chemicals DOI
Denis A. Kolykhalov, Anastasia N. Golysheva, Bogdan Ya. Karlinskii

et al.

Доклады Российской академии наук Химия науки о материалах, Journal Year: 2025, Volume and Issue: 517(1), P. 13 - 23

Published: Jan. 12, 2025

The effect of an aromatic triazole ring conjugated with a furan heterocycle on the stability under various reaction conditions was studied, and significant reduction in degree degradation electron-rich core hydrolysis ester group action model acid base organic solvents shown. lowest triazole-substituted 2-furoic achieved dioxane, as well polar aprotic (DMSO DMF). It shown that same conditions, tarring ester, which does not contain fragment, occurs.

Language: Английский

Citations

0
Bioorthogonal Cycloadditions of C3‐Trifluoromethylated 1,2,4‐Triazines with trans‐Cyclooctenes DOI Creative Commons
Veronika Šlachtová, Vladimir Motornov, Petr Beier

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(40)

Published: May 13, 2024

1,2,4-triazines are a valuable class of heterodienes that can be employed in inverse electron-demand Diels-Alder reactions. However, their broader application bioorthogonal chemistry is limited due to low reactivity. This article focuses on 3-(trifluoromethyl)-1,2,4-triazines, which efficiently prepared one-pot reaction from NH-1,2,3-triazoles. These triazines highly reactive reactions with strained cyclooctenes, giving second-order rate constants as high 230 M

Language: Английский

Citations

3
Harnessing the potential of acyl triazoles in bifunctional cobalt-catalyzed radical cross-coupling reactions DOI Creative Commons
Chang‐Yin Tan, Sungwoo Hong

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Aug. 13, 2024

Persistent radicals facilitate numerous selective radical coupling reactions. Here, we have identified acyl triazole as a new and versatile moiety for generating persistent intermediates through single-electron transfer processes. The efficient generation of these is facilitated by the formation substrate-coordinated cobalt complexes, which subsequently engage in cross-coupling Remarkably, triazole-coordinated complexes exhibit metal-hydride hydrogen atom (MHAT) capabilities with alkenes, enabling synthesis diverse ketone products without need external ligands. By leveraging effect, this catalytic approach also allows development other reactions two representative precursors. discovery triazoles effective substrates ligands catalysis, combined bifunctional nature system, opens up avenues design sustainable organic transformations. radical-mediated has emerged powerful tool forging C–C bonds. authors identify processes, context cobalt-catalysed carbon-carbon couplings under photoirradiation.

Language: Английский

Citations

2
Access to Bicyclo[3.1.0]hexane and Cyclopenta[c]pyrazole Scaffolds via Solvent-Directed Divergent Reactivity of 5-Iodotriazoles DOI

Xenia A. Barashkova,

Avetik G. Gevondian, Gennadij V. Latyshev

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(45), P. 9625 - 9630

Published: Nov. 6, 2024

Divergent access to bicyclo[3.1.0]hexane and cyclopenta[c]pyrazole scaffolds bearing azole azine units has been developed. The approach involves intramolecular cyclization of 5-iodo-1,2,3-triazoles acting as stable diazoimine precursors with concomitant noncatalytic (3 + 2)-cycloaddition. choice solvent allows control the outcome cascade transformation. developed procedure is simple cost-efficient allowed important heterocycles be obtained in one-pot various functional groups.

Language: Английский

Citations

1
NH-1,2,3-triazoles as versatile building blocks in denitrogenative transformations DOI Creative Commons
Vladimir Motornov, Petr Beier

RSC Advances, Journal Year: 2023, Volume and Issue: 13(49), P. 34646 - 34651

Published: Jan. 1, 2023

The utilization of NH-1,2,3-triazoles as easily accessible building blocks in denitrogenative ring cleavage transformations with electrophiles to provide multifunctionalized nitrogen heterocycles and N -alkenyl compounds is reviewed.

Language: Английский

Citations

3
Five-membered ring systems: With more than 1 N atom DOI
Larry Yet

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 211 - 257

Published: Jan. 1, 2024

Language: Английский

Citations

0
Denitrogenative Transformations of NH ‐ and N ‐Fluoroalkyl‐1,2,3‐triazoles DOI
Vladimir Motornov, Petr Beier

Published: Nov. 22, 2024

1,2,3-Triazoles with electron-acceptor groups on nitrogen, such as in situ acylated NH -triazoles or N -fluoroalkyl triazoles are amenable to denitrogenation thermally, using Brønsted Lewis acids, rhodium(II) catalysis. These cascade denitrogenations proceed via diazo intermediates followed by vinyl cations, rhodium carbene and lead various heterocyclic -alkenyl compounds.

Language: Английский

Citations

0
Allylboration of azole aldehydes: enantioselective synthesis of homoallylic azole alcohols and reconsideration of the mechanism of enantioselectivity DOI

Oleg A. Mikhaylov,

M. E. Gurskii,

E. Sh. Saigitbatalova

et al.

Russian Chemical Bulletin, Journal Year: 2024, Volume and Issue: 73(10), P. 2910 - 2920

Published: Oct. 1, 2024

Language: Английский

Citations

0
Synthesis of cyclic silyl enol ethers from α-Aryl-α-diazoketones: new building blocks for preparation of indanones and α,β-unsaturated ketones DOI
Yueqiang Liu, Sheng Zhang, Yang Li

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(24), P. 6117 - 6123

Published: Jan. 1, 2023

A new strategy for in situ generation of vinyl cation intermediates from α-diazocarbonyl compounds is described this paper.

Language: Английский

Citations

1