Radical coupling of arylthiodifluoroacetic acids and ethynylbenziodoxolone (EBX) reagents to access arylthiodifluoromethylated alkynes

A practical and efficient radical coupling of easily available arylthiodifluoroacetic acids and ethynylbenziodoxolone (EBX) reagents has been reported. Under transition metal-free conditions, aryl-substituted EBXs were converted to the corresponding ArSCF2-substituted alkynes in moderate to good yields, whereas TIPS-EBX underwent silver-catalyzed decarboxylative conditions to deliver the desired coupling products. The synthetic utility of this protocol was demonstrated through the transformation of resulting product to other ArSCF2 substituted alkynes and alkenes.

Automated summary

An efficient radical coupling method for arylthiodifluoroacetic acids and ethynylbenziodoxolone (EBX) reagents has been developed, providing moderate to good yields of ArSCF2-substituted alkynes. The synthetic utility of this protocol was demonstrated by transforming the resulting products into other ArSCF2-substituted alkynes and alkenes.