Sulfuryl Fluoride Mediated Conversion of Aldehydes to Nitriles |
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Authors: | Jitendra Gurjar Jorick Bater Prof?Dr Valery V Fokin |
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Institution: | University of Southern California, Bridge Institute and Loker Hydrocarbon Research Institute, 1002 Childs Way, Los Angeles, CA, 90089-3502 USA |
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Abstract: | 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. |
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Keywords: | bioorthogonal chemistry main group elements nitriles polyfunctional probes synthetic methods |
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