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2005•Organic LettersRequires access

Improved Method for the Iodine(III)-Mediated Preparation of Aryl Sulfonimidates

Anne Felim, A. Toussaint, Courtney R. Phillips, Dominique Leca, Anna L. Vagstad, Louis Fensterbank, Emmanuel Lacôte, Max Malacrìa

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Abstract

[reaction: see text] One-pot hypervalent iodine-mediated oxidations of arylsulfinamides to arylsulfonimidates is reported. Contrary to the case of alkylsulfinamides, use of iodosobenzene was not satisfactory. The reaction worked best with diacetoxyiodosobenzene (DIB) and a mild base (MgO). The influence of substituents on the iodine(III) reagent arene has been examined.

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[reaction: see text] One-pot hypervalent iodine-mediated oxidations of arylsulfinamides to arylsulfonimidates is reported. Contrary to the case of alkylsulfinamides, use of iodosobenzene was not satisfactory. The reaction worked best with diacetoxyiodosobenzene (DIB) and a mild base (MgO). The influence of substituents on the iodine(III) reagent arene has been examined.

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Available abstract

[reaction: see text] One-pot hypervalent iodine-mediated oxidations of arylsulfinamides to arylsulfonimidates is reported. Contrary to the case of alkylsulfinamides, use of iodosobenzene was not satisfactory. The reaction worked best with diacetoxyiodosobenzene (DIB) and a mild base (MgO). The influence of substituents on the iodine(III) reagent arene has been examined.

Key concepts: Hypervalent molecule, Iodine, Chemistry, Reagent, Aryl, Base (topology), Combinatorial chemistry, Medicinal chemistry

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