Synthesis of Sulfonyl Azides via Diazotransfer using an Imidazole-1-sulfonyl Azide Salt: Scope and 15N NMR Labeling Experiments
Marc Y. Stevens, Rajiv T. Sawant and Luke R. Odell*
*Organic Pharmaceutical Chemistry, Department of Medicinal Chemistry, Uppsala Biomedical Center, Uppsala University, P.O. Box 574, SE-751 23 Uppsala, Sweden, Email: luke.odellorgfarm.uu.se
M. Y. Stevens R. T. Sawant, L. R. Odell, J. Org. Chem., 2014, 79, 4826-4831.
DOI: 10.1021/jo500553q (free Supporting Information)
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Stable and easy to handle imidazole-1-sulfonyl azide hydrogen sulfate is an efficient reagent for the synthesis of sulfonyl azides from primary sulfonamides in an experimentally simple and high-yielding method without Cu salts. Furthermore, 15N NMR mechanistic studies show the reaction proceeds via a diazo transfer mechanism.
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A simple, reproducible and scalable synthesis of imidazole-1-sulfonyl azide hydrogen sulfate has been reported utilizing only EtOAc as a solvent. The product is readily isolated by filtration and has been demonstrated in the synthesis of up to 46 g of the diazotransfer reagent. DOI: 10.1021/acs.joc.6b00177
Luke R. Odell, April 25, 2016