Au-allenylidene promoted decarboxylative annulation to access unsaturated γ-lactams/lactones

Duan, Xuelun; Shi, Haotian; Yue, Yangyang; Song, Wangze

doi:10.1039/d4cc00200h

Chem. Commun.

2024

DOI: 10.1039/d4cc00200h

|View full text |Cite

Au-allenylidene promoted decarboxylative annulation to access unsaturated γ-lactams/lactones

Xuelun Duan,

Haotian Shi,

Yangyang Yue

et al.

Abstract: A novel Au-allenylidene promoted decarboxylative annulation by intramolecular α-nucleophilic addition has been disclosed. The unsaturated cyclic ethynylethylene carbamates/carbonates can be converted to unique nucleophiles attached with alkylidene ketenes by sequential...

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...

Article2

Relationship

Self Cite0

Independent2

Authors

Journals

Cited by 2 publications

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Bifunctional Ligand Enables Gold‐Catalyzed Propargyl C−H Functionalization via Reactive Gold Allenylidene Intermediate

Wei,

Jiang,

Jing

et al. 2024

Angewandte Chemie

View full text Add to dashboard Cite

Gold allenylidene species have been seldom exploited as reactive intermediates in synthetically versatile catalytic reactions. By employing alkynylbenziodoxoles as the substrates and bifunctional WangPhos as the metal ligand, this work demonstrated ready catalytic access to these intermediates of general substitution patterns and their electrophilic reactivities at the γ‐carbon center with a diverse range of nucleophiles. The reaction is driven by the reductive decomposition of the benziodoxole moiety and achieves the replacement of a propargylic proton with a N/O/C‐based nucleophile, hence realizing reactivity umpolung. Corroborated by DFT calculations, the reaction mechanism involves a mild propargylic deprotonation. In contrast to prior works employing a tertiary amine functionality, A barely BrØnsted‐basic amide group in WangPhos is surprisingly effective in deprotonation at the propargylic position under a gold‐ligand cooperation regime.

show abstract

Bifunctional Ligand Enables Gold‐Catalyzed Propargyl C−H Functionalization via Reactive Gold Allenylidene Intermediate

Wei,

Jiang,

Jing

et al. 2024

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

Bifunctional Ligand Enables Gold‐Catalyzed Propargyl C−H Functionalization via Reactive Gold Allenylidene Intermediate

Wei,

Jiang,

Jing

et al. 2024

Angew Chem Int Ed

View full text Add to dashboard Cite

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

hi@scite.ai

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

Henderson, NV 89052, USA

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.

Au-allenylidene promoted decarboxylative annulation to access unsaturated γ-lactams/lactones

Abstract: A novel Au-allenylidene promoted decarboxylative annulation by intramolecular α-nucleophilic addition has been disclosed. The unsaturated cyclic ethynylethylene carbamates/carbonates can be converted to unique nucleophiles attached with alkylidene ketenes by sequential...

Cited by 2 publications

References 29 publications

Bifunctional Ligand Enables Gold‐Catalyzed Propargyl C−H Functionalization via Reactive Gold Allenylidene Intermediate

Bifunctional Ligand Enables Gold‐Catalyzed Propargyl C−H Functionalization via Reactive Gold Allenylidene Intermediate

Bifunctional Ligand Enables Gold‐Catalyzed Propargyl C−H Functionalization via Reactive Gold Allenylidene Intermediate

Contact Info

Product

Resources

About