Gold(<i>I</i>)‐Catalyzed Reaction of 1‐(1‐Alkynyl)‐cyclopropyl Ketones with Vinyldiazo Ketones for Divergent Synthesis of Substituted Furanyl Heterocycles

Narode, Akshay Subhash; Liu, Rai‐Shung

doi:10.1002/ajoc.202300199

Asian J Org Chem

2023

DOI: 10.1002/ajoc.202300199

|View full text |Cite

Gold(I)‐Catalyzed Reaction of 1‐(1‐Alkynyl)‐cyclopropyl Ketones with Vinyldiazo Ketones for Divergent Synthesis of Substituted Furanyl Heterocycles

Akshay Subhash Narode

Rai‐Shung Liu

Abstract: Gold(I)-catalyzed reactions between 1-(1-alkynyl) cyclopropyl ketones and vinyldiazo ketones to produce substituted [(furan-3-yl)ethyl]-1H-pyrazol-5-yl)methanones are described. In this reaction sequence, we postulate vinyldiazo ketones to undergo a thermal cyclization to produce pyrazole intermediates that attack gold-containing all-carbon 1,4carbon dipoles to afford the observed products. An atypical N(1)-regioselectivity is also rationalized in this reaction model.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2024

Publication Types

Select...

Article4

Relationship

Self Cite0

Independent4

Authors

Journals

Cited by 4 publications

References 48 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Synthesis, structure, and catalytic performance of solvent induced zinc clusters in furan synthesis by cycloisomerization reaction

Farzaneh‐Bonab,

Bikas,

Noshiranzadeh

et al. 2024

Applied Organom Chemis

View full text Add to dashboard Cite

Two Zn(II) clusters were synthesized by the reaction of Zn(OAc)2·2H2O and 1,2‐bis(2‐hydroxy‐3‐methoxybenzylidene)hydrazine as a N2O4‐donor Schiff base ligand in 1:3 molar ratio. The reaction in methanol gave yellow‐brown needle crystals, while block yellow crystals were achieved in a mixture of methanol:water (50:50 v/v). Investigation of the crystals by single crystal X‐ray analysis showed that solvent has considerable effect on the structure and composition of the products. In methanol, two independent pentanuclear Zn(II) clusters with the same general formula of [Zn5(L)2(μ‐OAc)4(OAc)2(CH3OH)2] but different coordination environments around Zn(II) cores, and bridging mode of the acetate ligands are present in the unit cell. In a mixture of methanol:water, a pentanuclear cluster and a 1D coordination polymer with pentanuclear repetitive unit are simultaneously present in the crystal structure. These compounds were further characterized by spectroscopic techniques, and they were used as catalysts for intramolecular cycloisomerization of 1,4‐diphenylbut‐3‐yn‐1‐one. The results indicated that these Zn(II) clusters can efficiently produce 2,5‐diphenylfuran through catalytic cycloisomerization reaction.

show abstract

Synthesis, structure, and catalytic performance of solvent induced zinc clusters in furan synthesis by cycloisomerization reaction

Farzaneh‐Bonab,

Bikas,

Noshiranzadeh

et al. 2024

Applied Organom Chemis

View full text Add to dashboard Cite

show abstract

Ag(I)-Catalyzed Oxidative Cyclization of 1,4-Diynamide-3-ols with N-Oxide for Divergent Synthesis of 2-Substituted Furan-4-carboxamide Derivatives

Narode,

Barik,

Kuo

et al. 2024

J. Org. Chem.

View full text Add to dashboard Cite

This work reports Ag(I)-catalyzed oxidative cyclizations of 1,4-diynamide-3-ols with 8-methylquinoline oxide to form 2-substituted furan-4-carboxamides. The reaction chemoselectivity is distinct from that reported in previous work by Hashmi. We performed density functional theory calculations to elucidate our proposed mechanism after evaluation of the energy profiles of two possible pathways. In this Ag(I) catalysis, the calculations suggest that the amide and alkyne groups of the 3,3-dicarbonyl-2-alkyne intermediates tend to chelate with the Ag(I) catalyst, further inducing a formyl attack at the Ag(I)-π-alkyne moiety to deliver the observed products.

show abstract

Recent Advances in Gold-Catalyzed Transformations of Vinyldiazo Reagents

López,

Bernardo,

García-Martínez

et al. 2024

Synthesis

View full text Add to dashboard Cite

Since their discovery in 2011, gold-catalyzed transformations of vinyldiazo compounds have become an important synthetic tool, enabling the identification of new reaction patterns that have greatly expanded the versatility of these reagents. In this short review, we showcase the most relevant advances that have been made in this exciting area of research.1 Introduction2 Gold-Catalyzed Transformations of Vinyldiazo Compounds Involving Metal Carbene Intermediates2.1 Liu’s Seminal Work: Vinylogous Reactivity of Au(I) Vinyl Carbenes2.2 Gold-Catalyzed Reactions of Vinyldiazo Compounds with Alkenes2.3 Gold-Catalyzed Reactions of Vinyldiazo Compounds with Alkynes2.4 Gold-Catalyzed Reactions of Vinyldiazo Compounds with Allenes2.5 Gold-Catalyzed Reactions of Vinyldiazo Reagents with Aromatic Compounds2.6 Gold-Catalyzed Reactions of Vinyldiazo Compounds with Nitriles2.7 Gold-Catalyzed Diazo Cross-Couplings3 Gold-Catalyzed Transformations of Vinyldiazo Compounds That Do Not Involve Initial Dinitrogen Extrusion3.1 Gold-Catalyzed Formal [n+2] Cycloaddition Reactions through the Vinyl Moiety of Vinyldiazo Compounds3.2 Gold-Catalyzed Transformations of Vinyldiazo Compounds Involving Initial Activation of the Non-Diazo Reagent4 Conclusions

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.

Gold(I)‐Catalyzed Reaction of 1‐(1‐Alkynyl)‐cyclopropyl Ketones with Vinyldiazo Ketones for Divergent Synthesis of Substituted Furanyl Heterocycles

Cited by 4 publications

References 48 publications

Synthesis, structure, and catalytic performance of solvent induced zinc clusters in furan synthesis by cycloisomerization reaction

Synthesis, structure, and catalytic performance of solvent induced zinc clusters in furan synthesis by cycloisomerization reaction

Ag(I)-Catalyzed Oxidative Cyclization of 1,4-Diynamide-3-ols with N-Oxide for Divergent Synthesis of 2-Substituted Furan-4-carboxamide Derivatives

Recent Advances in Gold-Catalyzed Transformations of Vinyldiazo Reagents

Contact Info

Product

Resources

About