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September 10, 2025

Selectfluor-Mediated Oxidative S-Arylation of Sulfenamides with β-Naphthols for the Synthesis of Sulfilimines

Key Points

This method generates sulfilimines in good to high yields, with some achieving up to 95%.
The process includes 40 synthetic examples, showcasing a wide range of functional-group compatibility.
Employing Selectfluor allows for a streamlined procedure, which is easily scalable and time-efficient.
Significantly, it operates without the need for transition-metal catalysts or prefunctionalized arenes.

Abstract

We presented a Selectfluor-mediated direct oxidative S-arylation of N-acyl sulfenamides with naphthols via an oxidation to sulfinimidoyl fluoride/nucleophilic substitution cascade process. Notably, this methodology is time-efficient, operationally safe, and easily scalable without requiring prefunctionalized arenes or transition-metal catalysts. It exhibits excellent functional-group compatibility, providing a series of sulfilimines in good to high yields (40 examples, up to 95%).

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Cite This Study

Yao et al. (Wed,) studied this question.

synapsesocial.com/papers/68c1b81854b1d3bfb60ec3fb https://doi.org/https://doi.org/10.1021/acs.joc.5c01304

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