Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 25, Issue 8, Pages 1906-1909Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201805175
Keywords
bioorthogonal chemistry; main group elements; nitriles; polyfunctional probes; synthetic methods
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Funding
- National Science Foundation [CHE-1660373]
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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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