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Synfacts 2022; 18(01): 0035
DOI: 10.1055/s-0041-1737203
Metals in Synthesis

Synthesis of Sulfinamides, Sulfonimidamides, and Sulfonamides: A One-Pot Procedure to Rule them All

Contributor(s):
Martin Oestreich
,
Hendrik F. T. Klare
,
Benedikt Wolff
Lo PK. T, Willis MC. * University of Oxford, UK
Nickel(II)-Catalyzed Addition of Aryl and Hereoaryl Boroxines to the Sulfinylamine Reagent TrNSO: The Catalytic Synthesis of Sulfinamides, Sulfonimidamides, and Primary Sulfonamides.

J. Am. Chem. Soc. 2021;
143: 15576-15581
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Key words

boroxines - nickel catalysis - sulfinylamines - sulfonimidamides - trichloroisocyanuric acid

Significance

A one-pot approach for the synthesis of a variety of sulfinamides and derivatives is presented. Employing a commercially available catalyst and ligand, the catalyst loading can be lowered to 1 mol% for large-scale reactions. Trichloroisocyanuric acid (TCCA) is used as a mild, inexpensive, and safe chlorination agent.


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Comment

Boroxines are used as an alternative to moisture- and air-sensitive organometallic reagents, which often exclude a wide range of functional groups. Sulfonimidamides, primary sulfonamides, primary sulfinamides, and sulfonimidoyl fluorides are all obtained in moderate to good yields.


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Publication History

Article published online:
17 December 2021

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