1,3-Difunctionalization of Donor–Acceptor Cyclopropanes Enabled by Copper Nitrate: A Direct Approach to γ-Halonitrates DOI

Ruoxin Huang,

Mingchun Gao,

Zhenkun Yang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(45), P. 9659 - 9664

Published: Oct. 31, 2024

1,3-Difunctionalization of donor–acceptor cyclopropanes with copper nitrate and N-halosuccinimide was developed to efficiently afford γ-halonitrates. The pivotal factor this protocol lies in the dual role as a Lewis acid an ideal nitrooxy source. given approach features easy handling, good functional group compatibility, wide substrate scope. Furthermore, various transformations obtained γ-chloronitrates underscore remarkable synthetic potential inherent method.

Language: Английский

Electrochemical conversion of organic compounds and inorganic small molecules DOI

Wei-Mei Zeng,

Youai Qiu

Science China Chemistry, Journal Year: 2024, Volume and Issue: 67(10), P. 3223 - 3246

Published: July 9, 2024

Language: Английский

Citations

7

Electrochemical Formation of Oxazolines by 1,3-Oxyfluorination of Non-activated Cyclopropanes DOI

Madara Da̅rziņa,

Aigars Jirgensons

Organic Letters, Journal Year: 2024, Volume and Issue: 26(11), P. 2158 - 2162

Published: March 8, 2024

The C–C bond in non-activated cyclopropanes can be intramolecularly cleaved with an electrochemically generated amidyl radical forming oxazolines. In the presence of TBABF4, this provides 1,3-oxyfluorination products. cleavage cyclopropane proceeds inversion configuration, suggesting intramolecular homolytic substitution (SHi) mechanism. performance TBABF4 as efficient fluoride source was explained by accumulation BF4– anion at anode surface, which a carbocation is formed oxidation C-centered radical.

Language: Английский

Citations

5

Design, Synthesis, Nematicidal Activity Evaluation, and Mode of Action Study of Novel Trifluorobutene Ester Derivatives as Potential Nematicides DOI
Cheng Liu, Yadi Chen, Zhong Li

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 23, 2025

Crop protection globally is under threat from infections caused by plant-parasitic nematodes (PPNs). PPNs can wreak havoc on agricultural production. However, only limited nematicides are currently available, and the growing resistance problem a concern; therefore, novel urgently needed. Thirty-three trifluorobutene ester derivatives were synthesized, then their biological activity against Meloidogyne incognita was tested in this study. Among them, nine compounds exhibited excellent vitro bioactivity M. incognita; LC50/72h values reached 1.77-3.95 mg/L. In addition, derivative of active compound above containing piperazine ring significant vivo with an inhibition rate 77.3% at 1.25 mg/L matrix. The structure-activity relationships (SARs) all synthesized analyzed, further comparative molecular field analysis (CoMFA) calculated to discuss SAR profile. preliminary mechanisms action study suggested that some had great inhibitory effect egg hatching, motility, feeding ability, growth Caenorhabditis elegans. Meanwhile, effects biochemical indices related oxidative stress indicated two could significantly promote induce toxicity through damage.

Language: Английский

Citations

0

Recent Advances in Hypervalent Iodine Reagents and m-CPBA Mediated Oxidative Transformations DOI
Ravi Varala, Vittal Seema, Mohammed Amanullah

et al.

Current Organic Chemistry, Journal Year: 2024, Volume and Issue: 28(7), P. 489 - 509

Published: March 14, 2024

Abstract: Among the several peroxides available, meta-chloroperbenzoic acid (mCPBA) plays an efficient role of oxidizing reagent and is used for many oxidative transformations, such as oxidation various functional groups, carbon-carbon, carbon-hetero bond formation, heterocyclic ring heteroarylation, cross-coupling, lactonization, dearomatization, α-oxytosylation or α-acetoxylation, C-C activation in other miscellaneous reactions. The purpose this review to critically discuss significant contributions mCPBA along with hypervalent iodine/iodine reagents organic synthesis from mid-2015 date.

Language: Английский

Citations

3

Electrochemical 1,3-Alkyloxylimidation of Arylcyclopropane Radical Cations: Four-Component Access to Imide Derivatives DOI
Wei Zhou, Peng Chen,

Zi-Qiong Li

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(37), P. 6919 - 6924

Published: Sept. 11, 2023

Herein, a general electrochemical radical-cation-mediated four-component ring-opening 1,3-alkyloxylimidation of arylcyclopropanes, acetonitrile, carboxylic acids, and alcohols is described, providing facile sustainable approach to quickly construct structurally diverse imide derivatives from easily available raw materials in an operationally simple undivided cell. This metal-catalyst- oxidant-free single-electron oxidation strategy offers green alternative for the formation highly reactive cyclopropane-derived radical cations, this protocol features broad functional group tolerance.

Language: Английский

Citations

8

An Intermolecular Hydroarylation of Unactivated Arylcyclopropane via Re2O7/HFIP-Mediated Ring Opening DOI

Liqun Hu,

Yao Xiang,

Xiao‐Bing Lan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(10), P. 2085 - 2090

Published: March 5, 2024

In this paper, we describe a Re2O7-mediated ring-opening arylation of unactivated arylcyclopropane because its functionalization with various arenes via Friedel–Crafts-type reactivity. This protocol allows facile access to functionalized 1,1-diaryl alkanes and is characterized by broad substrate scope, mild reaction conditions, high efficiency, atom economy. Both density functional theory calculations deuterium labeling experiments were carried out justify the indispensable role HFIP in transformation pointed ring opening being rate-determining step.

Language: Английский

Citations

2

Cooperative Photoredox and N-Heterocyclic Carbene-Catalyzed Formal C-H Acylation of Cyclopropanes via Deconstruction-Reconstruction Strategy DOI Creative Commons
Fan Gao,

Tian Wang,

Xiaoyu Yan

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Cooperative NHC/photoredox catalyzed deconstruction–reconstruction of aryl cyclopropanes was described to access various α-acylated cyclopropane derivatives.

Language: Английский

Citations

2

SOMOphilic alkyne vs radical-polar crossover approaches: The full story of the azido-alkynylation of alkenes DOI Creative Commons
Julien Borrel, Jérôme Waser

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 701 - 713

Published: April 3, 2024

We report the detailed background for discovery and development of synthesis homopropargylic azides by azido-alkynylation alkenes. Initially, a strategy involving SOMOphilic alkynes was adopted, but only resulted in 29% yield desired product. By switching to radical-polar crossover approach after optimization, high (72%) azide reached. Full insights are given about factors that were essential success optimization process.

Language: Английский

Citations

1

Electrochemical deconstructive functionalization of arylcycloalkanes via fragmentation of anodically generated aromatic radical cations DOI Creative Commons
Hussain A. Maashi,

Abdulrahman H. Husayni,

James Harnedy

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

This highlight summarises electrochemical approaches for the deconstructive functionalization of arylcycloalkanes via fragmentation anodically generated aromatic radical cations.

Language: Английский

Citations

1

Electrochemical Synthesis of C(sp3)-Rich Heterocycles via Mesolytic Cleavage of Anodically Generated Aromatic Radical Cations DOI Creative Commons
Hussain A. Maashi,

Abdulrahman H. Husayni,

M Kharou

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(42), P. 9051 - 9055

Published: Oct. 21, 2024

Herein we report an electrochemical deconstructive functionalization approach for the synthesis of C(sp

Language: Английский

Citations

1