An Unexpected C‐S Bond Transformation with High Chemoselectivity for the Synthesis of Aryl‐Benzyl Sulfones

Metal-free oxidative sulfonylation strategy for the direct incorporation of sulfonyl units to access 3-sulfonyl succinimides, diarylmethyl sulfones and diarylsulfones via a free-radical pathway under aerobic conditions in aqueous media has been developed. Using easily accessible sulfonyl source, this methodology proceeds efficiently with a high degree of functional group compatibility under operationally simple reaction conditions. In this novel transformation with moderate to excellent yield, a green reaction system is established without the risk of metal contamination and inert atmosphere at room temperature. Mechanistic investigations revealed that sulfonyl radicals could be generated in situ from sulfonyl hydrazides in the presence of I 2 /TBHP under aerobic conditions.

show abstract

Metal‐Free Rapid Sulfonylation of para‐Quinone Methides and N‐Arylmaleimides with Sulfonyl Hydrazides via a Free‐Radical Pathway

Gairola

Peddinti

2022

Asian J Org Chem

View full text Add to dashboard Cite

show abstract

Triflic‐Acid‐Catalyzed Friedel‐Crafts Reaction for the Synthesis of Diaryl Sulfones

Falconnet¹,

Arndt

Hashmi

et al. 2022

Eur J Org Chem

View full text Add to dashboard Cite

The Friedel-Crafts sulfonylation for the synthesis of diaryl sulfones derivatives was achieved by using triflic acid (TfOH) as the acidic catalyst with aryl sulfonyl chlorides and arenes at elevated temperatures. Different sulfones could be synthesized with this method in good to excellent yield and with high selectivity. In contrast to the previous methodology reported for this sulfonylation, the catalyst and the excess of arene could be easily recovered and re-used in further batches.

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

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.

An Unexpected C‐S Bond Transformation with High Chemoselectivity for the Synthesis of Aryl‐Benzyl Sulfones

Cited by 2 publications

References 71 publications

Metal‐Free Rapid Sulfonylation of para‐Quinone Methides and N‐Arylmaleimides with Sulfonyl Hydrazides via a Free‐Radical Pathway

Metal‐Free Rapid Sulfonylation of para‐Quinone Methides and N‐Arylmaleimides with Sulfonyl Hydrazides via a Free‐Radical Pathway

Triflic‐Acid‐Catalyzed Friedel‐Crafts Reaction for the Synthesis of Diaryl Sulfones

Contact Info

Product

Resources

About