A solvent controlled three-component reaction of diazo compounds for the synthesis of hydrazone compounds under Brønsted acid catalysis

He, Hangli; Yan, Zhewei; Wang, Junyong; Yan, Qiongjiao; Wang, Wei; Wang, Haifeng; Chen, Fen‐Er

doi:10.1039/d2nj04983j

New J. Chem.

2022

DOI: 10.1039/d2nj04983j

|View full text |Cite

A solvent controlled three-component reaction of diazo compounds for the synthesis of hydrazone compounds under Brønsted acid catalysis

Hangli He

Zhewei Yan

Junyong Wang

et al.

Abstract: A novel Brønsted acid catalyzed three-component reaction of diazo compounds has been achieved from α-diazo ester, N-aminophthalimide and a solvent.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2023

2024

Publication Types

Select...

Article3

Relationship

Self Cite2

Independent1

Authors

Journals

Cited by 3 publications

References 48 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Rapid and General Access to α‐Halogenated Carbonyl Compounds Using Amidine Halide Salts as Halogen Sources under Mild Conditions

Li,

Luo,

Liu

et al. 2024

Eur J Org Chem

View full text Add to dashboard Cite

Rapid and efficient construction of α‐haloketones with diazo compounds and amidine·HX (X = Cl, Br, I) salts as halogen sources has been recognized as a simple and practical strategy. The reaction exhibits a broad scope and scalability, thereby enabling synthesis of a broad spectrum of functionally orchestrated α‐haloketones under mild and metal‐free conditions in a short time. Control experiments established the involvement of triffate 11 in the mechanism

show abstract

Rapid and General Access to α‐Halogenated Carbonyl Compounds Using Amidine Halide Salts as Halogen Sources under Mild Conditions

Li,

Luo,

Liu

et al. 2024

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

Al(OTf)₃-Catalyzed Regioselective N²–Arylation of Tetrazoles with Diazo Compounds

Zhou,

Li,

Zeng

et al. 2024

J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

Regioselective methods to access alkylated tetrazoles still remain a challenging goal. Herein, we describe a novel regioselective protocol for N2-arylation of tetrazoles with diazo compounds using inexpensive Al(OTf)3. This reaction could be conducted under mild conditions to access a diverse array of alkylated tetrazoles with 2-substituted tetrazoles as the major products, demonstrating a comprehensive range of substrate compatibility and excellent functional group compatibility. Mechanistic studies revealed a carbene-free process in this reaction procedure. Furthermore, the scale-up reaction and transformations of the N2-arylation of tetrazole products demonstrated the potential of this strategy.

show abstract

Substrate-Controlled Regioselective Alkylation of 4-Hydroxycoumarin with Diazo Compounds through TfOH Catalysis

Wang,

Xia,

et al. 2023

Synlett

Self Cite

View full text Add to dashboard Cite

Control of the regioselectivity of nucleophiles toward alkylating agents is a fundamental problem in heterocyclic chemistry. Substrate-controlled TfOH-catalyzed alkylation of 4-hydroxycoumarin with diazo compounds has been developed to provide rapid access to the C3- or O-alkylated 4-hydroxycoumarins with high efficiency. The regioselectivity can be determined by varying the electronic nature of the diazo substrates, especially those bearing a methylthio group.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

A solvent controlled three-component reaction of diazo compounds for the synthesis of hydrazone compounds under Brønsted acid catalysis

Abstract: A novel Brønsted acid catalyzed three-component reaction of diazo compounds has been achieved from α-diazo ester, N-aminophthalimide and a solvent.

Cited by 3 publications

References 48 publications

Rapid and General Access to α‐Halogenated Carbonyl Compounds Using Amidine Halide Salts as Halogen Sources under Mild Conditions

Rapid and General Access to α‐Halogenated Carbonyl Compounds Using Amidine Halide Salts as Halogen Sources under Mild Conditions

Al(OTf)₃-Catalyzed Regioselective N²–Arylation of Tetrazoles with Diazo Compounds

Substrate-Controlled Regioselective Alkylation of 4-Hydroxycoumarin with Diazo Compounds through TfOH Catalysis

Contact Info

Product

Resources

About

A solvent controlled three-component reaction of diazo compounds for the synthesis of hydrazone compounds under Brønsted acid catalysis

Abstract: A novel Brønsted acid catalyzed three-component reaction of diazo compounds has been achieved from α-diazo ester, N-aminophthalimide and a solvent.

Cited by 3 publications

References 48 publications

Rapid and General Access to α‐Halogenated Carbonyl Compounds Using Amidine Halide Salts as Halogen Sources under Mild Conditions

Rapid and General Access to α‐Halogenated Carbonyl Compounds Using Amidine Halide Salts as Halogen Sources under Mild Conditions

Al(OTf)3-Catalyzed Regioselective N2–Arylation of Tetrazoles with Diazo Compounds

Substrate-Controlled Regioselective Alkylation of 4-Hydroxycoumarin with Diazo Compounds through TfOH Catalysis

Contact Info

Product

Resources

About

Al(OTf)₃-Catalyzed Regioselective N²–Arylation of Tetrazoles with Diazo Compounds