Thionylimide Derivatives for Synthesis of Sulfonimidamides

BiPhONSO (1) and TrNSO (2) are utilized in the one-pot synthesis of sulfonimidamides. 1 gives the corresponding sulfonimidamides when treated with a Grignard reagent and an amine.¹⁾ The substitution style of the imine moiety varies depending on whether a primary or secondary amine is used. Furthermore, when the second nucleophile is replaced by an organometallic compound, the sulfoximine is afforded. On the other hand, 2 is known to give sulfonimidamide via a chlorinated intermediate just like 1,²⁾ and is also reported to allow decarboxylative insertion of a sulfinimide moiety to carboxylic acid through a photoredox reaction.³⁾

References

• 1) Harnessing Sulfinyl Nitrenes: A Unified One-Pot Synthesis of Sulfoximines and Sulfonimidamides
  • T. Q. Davies, M. J. Tilby, J. Ren, N. A. Parker, D. Skolc, A. Hall, F. Duarte, M. C. Willis, J. Am. Chem. Soc. 2020, 142, 15445.
• 2) One-Pot, Three-Component Sulfonimidamide Synthesis Exploiting the Sulfinylamine Reagent N-Sulfinyltritylamine, TrNSO
  • T. Q. Davies, A. Hall, M. C. Willis, Angew. Chem. Int. Ed. 2017, 56, 14937.
• 3) Photocatalytic Carboxylate to Sulfinamide Switching Delivers a Divergent Synthesis of Sulfonamides and Sulfonimidamides
  • J. A. Andrews, J. Kalepu, C. F. Palmer, D. L. Poole, K. E. Christensen, M. C. Willis, J. Am. Chem. Soc. 2023, 145, 21623.

Related Product

U0150

N-Sulfinyl-tert-butoxyamine (= tBuONSO)

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