4-Sulfanylmethyl- and 4-sulfonylmethyl-substituted N,N′-diarylimidazolium salts as new proligands in the synthesis of Pd complexes with N-heterocyclic carbenes

Shevchenko, M. A.; Pasyukov, D. V.; Minyaev, M. E.; Chernyshev, V. M.

doi:10.1007/s11172-024-4205-y

Russ Chem Bull

2024

DOI: 10.1007/s11172-024-4205-y

|View full text |Cite

4-Sulfanylmethyl- and 4-sulfonylmethyl-substituted N,N′-diarylimidazolium salts as new proligands in the synthesis of Pd complexes with N-heterocyclic carbenes

M. A. Shevchenko,

D. V. Pasyukov,

M. E. Minyaev

et al.

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 54 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

4‐Halomethyl‐Substituted Imidazolium Salts: A Versatile Platform for the Synthesis of Functionalized NHC Precursors

Pasyukov,

Shevchenko,

Minyaev

et al. 2024

Chemistry An Asian Journal

View full text Add to dashboard Cite

N,Nʹ‐Diarylimidazolium salts containing haloalkyl functional groups that are reactive with various nucleophiles are considered to be promising reagents for the preparation of functionalized N‐heterocyclic carbene (NHC) ligands, which are in demand in catalysis, materials science, and biomedical research. Recently, 4‐chloromethyl‐functionalized N,N'‐diarylimidazolium salts became readily available via the condensation of N,N'‐diaryl‐2‐methyl‐1,4‐diaza‐1,3‐butadienes with ethyl orthoformate and Me3SiCl, but these compounds were found to have insufficient reactivity in reactions with many nucleophiles. These chloromethyl salts were studied as precursors in the synthesis of bromo‐ and iodomethyl‐functionalized imidazolium salts by halide anion exchange. The 4‐ICH2‐functionalized products were found to be unstable, whereas a series of novel 4‐bromomethyl functionalized N,N'‐diarylimidazolium salts were obtained in good yields. These bromomethyl‐functionalized imidazolium salts were found to be significantly more reactive towards various N, O and S nucleophiles than the chloromethyl counterparts and enabled the preparation of previously inaccessible heteroatom‐functionalized imidazolium salts, some of which were successfully used as NHC proligands in the preparation of Pd/NHC and Au/NHC complexes.

show abstract

4‐Halomethyl‐Substituted Imidazolium Salts: A Versatile Platform for the Synthesis of Functionalized NHC Precursors

Pasyukov,

Shevchenko,

Minyaev

et al. 2024

Chemistry An Asian Journal

View full text Add to dashboard Cite

show abstract

Cu/NHC Complexes with 4-Sulfanyl- and 4-Sulfonylimidazole in Carboxylation Reactions

Pasyukov,

Shevchenko,

Malakhov

2024

Russ J Gen Chem

View full text Add to dashboard Cite

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.

4-Sulfanylmethyl- and 4-sulfonylmethyl-substituted N,N′-diarylimidazolium salts as new proligands in the synthesis of Pd complexes with N-heterocyclic carbenes

Cited by 2 publications

References 54 publications

4‐Halomethyl‐Substituted Imidazolium Salts: A Versatile Platform for the Synthesis of Functionalized NHC Precursors

4‐Halomethyl‐Substituted Imidazolium Salts: A Versatile Platform for the Synthesis of Functionalized NHC Precursors

Cu/NHC Complexes with 4-Sulfanyl- and 4-Sulfonylimidazole in Carboxylation Reactions

Contact Info

Product

Resources

About