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; Nicholas Ball

doi:10.26434/chemrxiv.12026811.v1

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

25 March 2020, Version 1

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Abstract

A method to activate sulfamoyl fluorides, fluorosulfates, and sulfonyl fluorides with calcium triflimide, and DABCO for SuFEx with amines is described. The reaction was applied to a diverse set of sulfamides, sulfamates, and sulfonamides at room temperature under mild conditions. Additionally, we highlight the application of this transformation to parallel medicinal chemistry to generate a broad array of nitrogen-based S(VI) compounds.

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SuFEx

sulfur-fluoride exchange

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Mahapatra Woroch SI Final

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PMC Final 23 March amEnde (1)

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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, Nicholas D. Ball journal article

Organic Letters , Volume 22, Issue 11

Online publication date: May 27, 2020

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Mar 25, 2020 Version 1

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The content is available under CC BY NC ND 4.0

DOI

10.26434/chemrxiv.12026811.v1

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No conflict of Interest

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

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