A Concise Route to 2-Sulfonylacetonitriles from Sodium Metabisulfite

A three-component reaction of aryldiazonium tetrafluoroborates, sodium metabisulfite, and 3-azido-2-methylbut-3-en-2-ol under mild conditions is described. By using abundant and cheap sodium metabisulfite as the sulfur dioxide surrogate, this protocol features good functional group compatibility, affording 2-arylsulfonylacetonitriles in moderate to good yields. The reaction proceeds smoothly at room temperature without the need of any catalysts or additives. Moreover, the synthetic utility of this method is demonstrated by the transformation of 2-arylsulfonylacetonitrile into 2-arylsulfonyl acetamide and 2-arylsulfonylethylamine.

Automated summary

This study describes a three-component reaction using sodium metabisulfite as a sulfur dioxide surrogate to synthesize 2-arylsulfonylacetonitriles under mild conditions. The reaction shows good functional group compatibility and proceeds smoothly at room temperature without the need of any catalyst or additive. The synthetic utility of this method is further demonstrated by the transformation of the product into other useful compounds.