Catalytic hydrosilylation of 1,3-diynes towards (E)-2-silylbut-1-en-3-ynes, (E,E)-2,3-disilylbuta-1,3-dienes and (E,E)-2-silyl1-3-silyl2buta-1,3-dienes

Stefanowska-Kątna, Kinga; Szymkowiak, Michał; Nagórny, Jakub; Czapik, Agnieszka; Walkowiak, Jędrzej; Franczyk, Adrian

doi:10.1016/j.jcat.2024.115519

Journal of Catalysis

2024

DOI: 10.1016/j.jcat.2024.115519

|View full text |Cite

Catalytic hydrosilylation of 1,3-diynes towards (E)-2-silylbut-1-en-3-ynes, (E,E)-2,3-disilylbuta-1,3-dienes and (E,E)-2-silyl1-3-silyl2buta-1,3-dienes

Kinga Stefanowska-Kątna,

Michał Szymkowiak,

Jakub Nagórny

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 47 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Synthesis of silylbut-1-en-3-ynes and buta-1,3-dienes as building blocks via hydrosilylation of 1,4-bis(trimethylsilyl)buta-1,3-diyne

Stefanowska-Kątna,

Walkowiak,

Franczyk

2024

Sci Rep

View full text Add to dashboard Cite

The selective and efficient synthesis of (E)-1,2,4-trisilylbut-1-en-3-ynes obtained via Pt-catalyzed hydrosilylation of 1,4-bis(trimethylsilyl)buta-1,3-diyne is described. Optimized reaction conditions (Pt(PPh3)4) or Pt2(dvs)3, 100 °C, toluene, 18 h) yielded compounds with high isolation yields (76–95%). The modification of (E)-1,2,4-trisilylbut-1-en-3-ynes was further tested in protodesilylation, halodesilylation, hydrosilylation, and Pd-based cross-coupling reactions, resulting in a broad spectrum of new products. These compounds represent new families of buta-1,3-dienes, (E,E)-2,3-bissilylbuta-1,3-dienes, (E,E)-1,2,3-trisilylbuta-1,3-dienes, and (E,E)-1,2,3-trisilylbuta-1,3-dienes, which are ideally suited to silicon-based transformations and are perfect models for the investigation of the reactivity of one silyl group in the presence of another.

show abstract

Synthesis of silylbut-1-en-3-ynes and buta-1,3-dienes as building blocks via hydrosilylation of 1,4-bis(trimethylsilyl)buta-1,3-diyne

Stefanowska-Kątna,

Walkowiak,

Franczyk

2024

Sci Rep

View full text Add to dashboard Cite

show abstract

Modular Synthesis of New Metalloid-Substituted Olefins from Diboryl(Silyl)Ethenes via Suzuki–Miyaura Reactions

Sokolnicki,

Stefanowska-Kątna,

Czapik

et al. 2024

IJMS

View full text Add to dashboard Cite

A novel approach towards synthesizing new metalloid-substituted olefins has been accomplished by transforming (E)-1,2-diboryl-1-silylethenes through two consecutive Suzuki–Miyaura coupling reactions. This methodology provides an effective and selective way to obtain new, structurally different products, such as (E)-1-silyl-1-boryl-2-arylethens, (1E,3E)-1-silyl-1-boryl-2-alkenylethens, and (E)-1-silyl-1-aryl1-2-aryl2ethenes, which are difficult to synthesize through hydrometallation reactions and related processes. Due to the presence of reactive motifs (silyl group, Bpin moiety, and Csp2-H bond) in the structure of the final products, these molecules might be considered powerful building blocks in modern chemistry. With the aid of demetallation and cross-coupling reactions, they might be further functionalized into several invaluable chemicals, i.e., tetrasubstituted olefins (anti-cancer drugs, fluorescence materials), compounds with high π-conjugation, and polymers.

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.

Catalytic hydrosilylation of 1,3-diynes towards (E)-2-silylbut-1-en-3-ynes, (E,E)-2,3-disilylbuta-1,3-dienes and (E,E)-2-silyl1-3-silyl2buta-1,3-dienes

Cited by 2 publications

References 47 publications

Synthesis of silylbut-1-en-3-ynes and buta-1,3-dienes as building blocks via hydrosilylation of 1,4-bis(trimethylsilyl)buta-1,3-diyne

Synthesis of silylbut-1-en-3-ynes and buta-1,3-dienes as building blocks via hydrosilylation of 1,4-bis(trimethylsilyl)buta-1,3-diyne

Modular Synthesis of New Metalloid-Substituted Olefins from Diboryl(Silyl)Ethenes via Suzuki–Miyaura Reactions

Contact Info

Product

Resources

About