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
DOI:
10.1021/jacs.1c08052
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.
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.
