Nickel-free cross-electrophile coupling of unactivated alkyl bromides with thiosulfonates and sulfinyl sulfones

Fan, Qiujin; Zhao, Yanchuang; Liang, Jintao; Zhang, Yan; Xu, Yuenian; Zhang, Qingqing; Zhu, Hua; Jiang, Min; Shao, Xinxin

doi:10.1039/d4qo00023d

Org. Chem. Front.

2024

DOI: 10.1039/d4qo00023d

|View full text |Cite

Nickel-free cross-electrophile coupling of unactivated alkyl bromides with thiosulfonates and sulfinyl sulfones

Qiujin Fan,

Yanchuang Zhao,

Jintao Liang

et al.

Abstract: An unusual zinc-promoted reductive coupling between alkyl bromides and thiosulfonates under nickel-free conditions is described. This pracitical strategy provides an attractive approach to access a series of structure-varied sulfides which...

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 57 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Bifunctionalization of α-Bromophenone: An Access to Functionalized β-Keto Thiosulfones

Wen,

Li,

Peng

et al. 2024

J. Org. Chem.

View full text Add to dashboard Cite

A simple and high-yielding strategy to produce a variety of β-keto sulfides using asymmetrical and symmetrical thiosulfonates with ketones under mild conditions is reported. It was found that the various substituted compounds, with both electron-withdrawing and electron-donating substituents, afforded a wide range of β-keto thiosulfones (α-thioaryl-β-keto sulfones) in moderate to high yields. The transformations were reliable at the gram-scale, thus illustrating their efficiency and practicality. A plausible mechanism for the protocol is also proposed.

show abstract

Bifunctionalization of α-Bromophenone: An Access to Functionalized β-Keto Thiosulfones

Wen,

Li,

Peng

et al. 2024

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

Cross-Electrophile Couplings of Benzyl Sulfonium Salts with Thiosulfonates via C–S Bond Activation

Hu,

Chen,

Zhu

et al. 2024

J. Org. Chem.

View full text Add to dashboard Cite

A zinc-mediated cross-electrophile coupling of benzyl sulfonium salts with thiosulfonates via C−S bond cleavage was achieved. The reductive thiolation proceeded well under transition metal-free conditions to afford the desired benzyl sulfides in good yields, exhibiting both broad substrate scope and good functionality tolerance. In addition, the reaction could be applied to the use of selenosulfonate as an effective selenylation agent and be subjected to scale-up synthesis.

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.

Nickel-free cross-electrophile coupling of unactivated alkyl bromides with thiosulfonates and sulfinyl sulfones

Abstract: An unusual zinc-promoted reductive coupling between alkyl bromides and thiosulfonates under nickel-free conditions is described. This pracitical strategy provides an attractive approach to access a series of structure-varied sulfides which...

Cited by 2 publications

References 57 publications

Bifunctionalization of α-Bromophenone: An Access to Functionalized β-Keto Thiosulfones

Bifunctionalization of α-Bromophenone: An Access to Functionalized β-Keto Thiosulfones

Cross-Electrophile Couplings of Benzyl Sulfonium Salts with Thiosulfonates via C–S Bond Activation

Contact Info

Product

Resources

About