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Sulfuryl Fluoride Mediated Conversion of Aldehydes to Nitriles
Author(s) -
Gurjar Jitendra,
Bater Jorick,
Fokin Valery V.
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201805175
Subject(s) - chemistry , nitrile , hydroxylamine , organic chemistry , derivatization , selectivity , catalysis , alkyne , fluoride , azide , combinatorial chemistry , inorganic chemistry , high performance liquid chromatography
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.