Copper-catalyzed multicomponent assembly of γ-butenolides via the interception of carbonyl ylides with iminium ions DOI
Mengchu Zhang, Sifan Yu,

Ruyu Hua

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 21(4), P. 783 - 788

Published: Dec. 20, 2022

A Cu(I)-catalyzed three-component reaction of cyclopropenes, enamines and aldehydes has been realized. This proceeds via the interception carbonyl oxonium ylide intermediates with α, β-unsaturated iminium ions that are in situ generated from under catalysis Cu(MeCN)4PF6, leading to desired γ-butenolide derivatives good yields moderate diastereoselectivities. Access these tethered ketone alkynal groups will expand structural diversity multi-substituted butenolides.

Language: Английский

Photoinduced [4 + 2]-cycloaddition reactions of vinyldiazo compounds for the construction of heterocyclic and bicyclic rings DOI Creative Commons
Ming Bao, Arnold R. Romero Bohórquez, Hadi D. Arman

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(30), P. 12042 - 12046

Published: Jan. 1, 2024

Under blue light vinyldiazoacetate reagents selectively form unstable cyclopropenes that undergo intermolecular cycloaddition reactions at a faster rate than their competitive ene dimerization.

Language: Английский

Citations

9
Copper-Catalyzed Hydroamination: Enantioselective Addition of Pyrazoles to Cyclopropenes DOI
Minghao Wang,

Julie Simon,

Mengfei Xu

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(27), P. 14573 - 14580

Published: June 30, 2023

Chiral N-cyclopropyl pyrazoles and structurally related heterocycles are prepared using an earth-abundant copper catalyst under mild reaction conditions with high regio-, diastereo-, enantiocontrol. The observed N2:N1 regioselectivity favors the more hindered nitrogen of pyrazole. Experimental DFT studies support a unique mechanism that features five-centered aminocupration.

Language: Английский

Citations

19
β-Thioamide Sulfone Enabled Copper-Catalyzed Ring-Opening/Sulfonylation of Cyclopropenes: Access to Alkyl Aryl Sulfones DOI

Arshad Ali,

C.‐S. CHUNG, Jingru Wang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 9, 2025

Sulfone motifs play important roles in bioactive compounds and functional materials. The development of efficient methodologies for constructing sulfonyl-containing has thus attracted considerable attention. Here, we introduce a protocol the preparation alkyl aryl sulfones under mild conditions. This employs β-thioamide sulfone as novel motif donor. It forms sulfinates situ basic conditions, which then undergo cross-coupling with intermediates that were generated from ligand-free copper-catalyzed cyclopropenes (CPEs) ring opening.

Language: Английский

Citations

0
The literature of heterocyclic chemistry, part XXII, 2022 DOI
Галина А. Газиева, Yu. B. Evdokimenkova, N. O. Soboleva

et al.

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

Published: Jan. 1, 2025

Language: Английский

Citations

0
Preparation, spectral characterization, in silico ADME studies, molecular docking, and antioxidant activity of some derivatives of the Oxazepine symmetrical dimers DOI
Abdul Jabbar, Manaf A. Guma,

Rasim Farraj Muslim

et al.

AIP conference proceedings, Journal Year: 2025, Volume and Issue: 3303, P. 040009 - 040009

Published: Jan. 1, 2025

Language: Английский

Citations

0
Enantioselective Cobalt(III)-Catalyzed [4 + 1] Annulation of Benzamides: Cyclopropenes as One-Carbon Synthons DOI Creative Commons
Lenin Kumar Verdhi, Matthew D. Wodrich, Nicolai Cramer

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: April 28, 2025

A chiral cyclopentadienyl cobalt(III)-catalyzed enantioselective [4 + 1] annulation of N-chlorobenzamides with cyclopropenes is reported. The cobalt catalyst engages in the C-H activation as well promotes C-C bond cleavage cyclopropene, rendering it a one-carbon unit for annulation. reaction efficiently constructs biologically relevant isoindolinones selectivities up to 99:1 er and >20:1 E/Z ratios. cobalt(III) displays unique orthogonal reactivity profile delivering products, whereas its rhodium(III) homologue more classical 2] pattern. Computational studies reveal origin these divergences.

Language: Английский

Citations

0
Temperature-Dependent Divergent Cyclopentadiene Synthesis through Cobalt-Catalyzed C–C Activation of Cyclopropenes DOI

Tianlong Zeng,

Ying Li,

Ruobin Wang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(16), P. 3413 - 3418

Published: April 15, 2024

We report a temperature-dependent divergent approach to synthesize multisubstituted cyclopentadienes through cobalt-catalyzed carbon–carbon (C–C) bond activation of cyclopropenes and ring expansion with internal alkynes. By employing different heating procedures, two cyclopentadiene substitution isomers were efficiently selectively constructed. This reaction does not require preactivation the metal catalyst or additional reducing reagents. Preliminary mechanistic investigations suggest that key steps are oxidative addition cyclopropene cobalt catalyst, followed by alkyne insertion 1,5-ester shift.

Language: Английский

Citations

3
Stereoselective synthesis of 1,3- and 1,4-dicarbonyl-alkenes from cyclopropenes in a catalytic zinc system DOI

Jia‐Bin Han,

Yu Liu,

Xiaoyan Yang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(19), P. 4887 - 4894

Published: Jan. 1, 2023

This work describes a dual catalytic system for selective synthesis of α-allyl-1,3-ketoaldehydes and α-vinyl-1,4-ketoaldehydes through cascade reactions hydroxyl substituted aromatic enaminones with cyclopropenes under zinc promoted conditions.

Language: Английский

Citations

8
Heterocycles from cyclopropenones DOI Creative Commons
Ashraf A. Aly, Alaa A. Hassan, Sara M. Mostafa

et al.

RSC Advances, Journal Year: 2022, Volume and Issue: 12(29), P. 18615 - 18645

Published: Jan. 1, 2022

Great attention has been paid to cyclopropenones as they are present in many natural sources.

Language: Английский

Citations

14
Photocatalyzed Direct C(sp3)–H Alkenylation of Unactivated Alkanes via Tandem C–C Activation of Cyclopropenes DOI
Sourabh Biswas, Debabrata Das,

Koustav Pal

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12421 - 12431

Published: Aug. 16, 2024

A highly adaptable method has been developed for the alkenylation of a broad spectrum inert alkanes, employing milder reaction conditions. Tetrabutylammonium decatungstate (TBADT) serves as photocatalyst hydrogen atom transfer (HAT), instigating formation transient alkyl radicals through C(sp3)–H functionalization. These exhibit regioselective addition to cyclopropenes, followed by subsequent activation C–C bonds, forming corresponding vinylated derivatives. This methodology accommodates diverse unreactive bond motifs and multisubstituted enabling efficient synthesis functionalized olefins with high diastereoselectivity.

Language: Английский

Citations

2