Sulfuryl Fluoride Mediated Conversion of Aldehydes to Nitriles

Aliphatic, aromatic, and heteroaromatic aldehydes were readily converted to corresponding nitriles in a one‐pot reaction sequence with hydroxylamine and sulfuryl fluoride. The reaction proceeds at room temperature, does not require metal catalysts and special precautions, and produces nitriles in excellent yields. It is compatible with a variety of functional groups, can be performed in aqueous and organic solvents, and is readily scalable to multigram quantities. Mild conditions and high selectivity of the reaction enabled the construction of polyfunctional probes containing nitrile, alkyne, azide, and fluorosulfate groups for further orthogonal derivatization. Aldehydes were readily converted to the corresponding nitriles in excellent yields by using hydroxylamine and sulfuryl fluoride in a one‐pot reaction sequence under mild conditions and in the absence of metal catalysts. The reaction is compatible with several functional groups, can be scaled up and performed in aqueous solutions. The method allowed for the construction of polyfunctional probes containing nitrile, alkyne, azide, and fluorosulfate groups for further orthogonal derivatization.