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Literature DB >> 16408909

Improved method for the iodine(III)-mediated preparation of aryl sulfonimidates.

Anne Felim¹, Aurélie Toussaint, Courtney R Phillips, Dominique Leca, Anna Vagstad, Louis Fensterbank, Emmanuel Lacôte, Max Malacria.

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.

Entities: Chemical

Year: 2006 PMID： 16408909 DOI： 10.1021/ol052790t

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

5 in total

1. SuFEx Chemistry of Thionyl Tetrafluoride (SOF₄ ) with Organolithium Nucleophiles: Synthesis of Sulfonimidoyl Fluorides, Sulfoximines, Sulfonimidamides, and Sulfonimidates.

Authors: Bing Gao; Suhua Li; Peng Wu; John E Moses; K Barry Sharpless
Journal: Angew Chem Int Ed Engl Date: 2018-01-16 Impact factor: 15.336

Improved method for the iodine(III)-mediated preparation of aryl sulfonimidates.

1. SuFEx Chemistry of Thionyl Tetrafluoride (SOF₄ ) with Organolithium Nucleophiles: Synthesis of Sulfonimidoyl Fluorides, Sulfoximines, Sulfonimidamides, and Sulfonimidates.

2. Modular Two-Step Route to Sulfondiimidamides.

3. A Silyl Sulfinylamine Reagent Enables the Modular Synthesis of Sulfonimidamides via Primary Sulfinamides.

4. A New, Practical One-Pot Synthesis of Unprotected Sulfonimidamides by Transfer of Electrophilic NH to Sulfinamides.

5. Modern Stereoselective Synthesis of Chiral Sulfinyl Compounds.

Improved method for the iodine(III)-mediated preparation of aryl sulfonimidates.

1. SuFEx Chemistry of Thionyl Tetrafluoride (SOF4 ) with Organolithium Nucleophiles: Synthesis of Sulfonimidoyl Fluorides, Sulfoximines, Sulfonimidamides, and Sulfonimidates.

2. Modular Two-Step Route to Sulfondiimidamides.

3. A Silyl Sulfinylamine Reagent Enables the Modular Synthesis of Sulfonimidamides via Primary Sulfinamides.

4. A New, Practical One-Pot Synthesis of Unprotected Sulfonimidamides by Transfer of Electrophilic NH to Sulfinamides.

5. Modern Stereoselective Synthesis of Chiral Sulfinyl Compounds.

1. SuFEx Chemistry of Thionyl Tetrafluoride (SOF₄ ) with Organolithium Nucleophiles: Synthesis of Sulfonimidoyl Fluorides, Sulfoximines, Sulfonimidamides, and Sulfonimidates.