SuFEx Activation with Ca(NTf₂)₂: A Unified Strategy to Access Sulfamides, Sulfamates, and Sulfonamides from S(VI) Fluorides

Subham Mahapatra, Cristian P. Woroch, Todd W. Butler, Sabrina N. Carneiro, Sabrina C. Kwan, Samuel R. Khasnavis, Junha Gu, Jason K. Dutra, Beth C. Vetelino, Justin Bellenger, Christopher W. am Ende* and Nicholas D. Ball*

*Pfizer, Eastern Point Road, Groton, Connecticut 06340; Pomona College, 645 North College Avenue, Claremont, California 91711, United States, Email: christopher.amendepfizer.com, nicholas.ballpomona.edu

S. Mahapatra, C. P. Woroch, T. W. Butler, S. N. Carneiro, S. C. Kwan, S. R. Khasnavis, J. Gu, J. K. Dutra, B. C. Vetelino, J. Bellenger, C. W. am Ende, N. D. Ball, Org. Lett., 2020, 22, 4389-4394.

DOI: 10.1021/acs.orglett.0c01397

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Abstract

The combination of calcium triflimide and DABCO activates sulfamoyl fluorides, fluorosulfates, and sulfonyl fluorides for SuFEx with amines to provide a diverse set of sulfamides, sulfamates, and sulfonamides at room temperature under mild conditions.

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Key Words

sulfamides, sulfamates, sulfonamides

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ID: J54-Y2020