Borylated cyclobutanes <i>via</i> thermal [2 + 2]-cycloaddition

Prysiazhniuk, Kateryna; Polishchuk, Oleksandr; Shulha, Stanislav; Gudzikevych, Kyrylo; Datsenko, Oleksandr P.; Kubyshkin, Vladimir; Mykhailiuk, Pavel K.

doi:10.1039/d3sc06600b

Chem. Sci.

2024

DOI: 10.1039/d3sc06600b

|View full text |Cite

Borylated cyclobutanes via thermal [2 + 2]-cycloaddition

Kateryna Prysiazhniuk,

Oleksandr Polishchuk,

Stanislav Shulha

et al.

Abstract: A one-step approach to borylated cyclobutanes from amides of carboxylic acids and vinyl boronates is elaborated. The reaction proceeds via the thermal [2 + 2]-cycloaddition of in situ-generated keteniminium salts.

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...

Article1

Relationship

Self Cite0

Independent1

Authors

Journals

Cited by 1 publication

References 48 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Regioselective Synthesis of α-Vinyl Boronates via a Pd-Catalyzed Mizoroki–Heck Reaction

Chen,

Isbrandt,

Newman

2024

Org. Lett.

View full text Add to dashboard Cite

We report a palladium-catalyzed synthesis of α-vinyl boronates via a regioselective Mizoroki−Heck reaction between aryl triflates and vinyl boronates. This selectivity is achieved by the use of a 1,5-diaza-3,7-diphosphacyclooctane (P 2 N 2 ) ligand, which results in minimal formation of the more commonly observed (linear) β-product. The choice of base, solvent, and presence of water are shown to be critical for controlling this outcome, with organic bases, nonpolar solvents, and anhydrous conditions favoring the Heck product and suppressing the competitive Suzuki−Miyaura coupling product.

show abstract

Regioselective Synthesis of α-Vinyl Boronates via a Pd-Catalyzed Mizoroki–Heck Reaction

Chen,

Isbrandt,

Newman

2024

Org. Lett.

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.

Borylated cyclobutanes via thermal [2 + 2]-cycloaddition

Abstract: A one-step approach to borylated cyclobutanes from amides of carboxylic acids and vinyl boronates is elaborated. The reaction proceeds via the thermal [2 + 2]-cycloaddition of in situ-generated keteniminium salts.

Cited by 1 publication

References 48 publications

Regioselective Synthesis of α-Vinyl Boronates via a Pd-Catalyzed Mizoroki–Heck Reaction

Regioselective Synthesis of α-Vinyl Boronates via a Pd-Catalyzed Mizoroki–Heck Reaction

Contact Info

Product

Resources

About