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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
Working Paper
This content is an early or alternative research output and has not been peer-reviewed by Cambridge University Press at the time of posting.

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.

Keywords

SuFEx
sulfur-fluoride exchange
Sulfur(VI) fluorides
sulfamoyl fluorides
fluorosulfates
sulfonyl fluorides
Calcium triflimide
sulfamides
sulfamates
sulfonamides
DABCO

Supplementary materials

Title
Description
Actions
Title
Mahapatra Woroch SI Final
Description
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Title
PMC Final 23 March amEnde (1)
Description
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Now Published

SuFEx Activation with Ca(NTf2)2: A Unified Strategy to Access Sulfamides, Sulfamates, and Sulfonamides from S(VI) Fluorides [opens in a new tab]
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

Version History

Mar 25, 2020 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv.12026811.v1
D O I: 10.26434/chemrxiv.12026811.v1 [opens in a new tab]

Author’s competing interest statement

No conflict of Interest

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