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Literature DB >> 28809121

The Synthesis of Trifluoromethyl-sulfonimidamides from Sulfinamides.

Charlotte S Richards-Taylor¹, Carolina Martínez-Lamenca¹, Joseph E Leenaerts¹, Andres A Trabanco², Daniel Oehlrich¹.

Abstract

A general synthesis of CF3-sulfonimidamides from sulfinamides under both batch and continuous flow conditions is described. The reaction proceeds via a sulfonimidoyl fluoride intermediate. A reaction scope showing good group variation on the substituents of both nitrogen atoms is also presented.

Entities: Chemical

Year: 2017 PMID： 28809121 DOI： 10.1021/acs.joc.7b01628

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

9 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

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

Authors: Mingyan Ding; Ze-Xin Zhang; Thomas Q Davies; Michael C Willis
Journal: Org Lett Date: 2022-02-21 Impact factor: 6.072

3. CF₃SO₂X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF₃SO₂Na.

Authors: Hélène Guyon; Hélène Chachignon; Dominique Cahard
Journal: Beilstein J Org Chem Date: 2017-12-19 Impact factor: 2.883

4. Additions to N-Sulfinylamines as an Approach for the Metal-free Synthesis of Sulfonimidamides: O-Benzotriazolyl Sulfonimidates as Activated Intermediates.

Authors: Maximilian Bremerich; Christian M Conrads; Tim Langletz; Carsten Bolm
Journal: Angew Chem Int Ed Engl Date: 2019-11-11 Impact factor: 15.336

The Synthesis of Trifluoromethyl-sulfonimidamides from Sulfinamides.

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

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

3. CF₃SO₂X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF₃SO₂Na.

4. Additions to N-Sulfinylamines as an Approach for the Metal-free Synthesis of Sulfonimidamides: O-Benzotriazolyl Sulfonimidates as Activated Intermediates.

5. Modular Sulfondiimine Synthesis Using a Stable Sulfinylamine Reagent.

6. Modern Stereoselective Synthesis of Chiral Sulfinyl Compounds.

Review 7. Direct synthesis of sulfenamides, sulfinamides, and sulfonamides from thiols and amines.

8. Exploration of Novel Chemical Space: Synthesis and in vitro Evaluation of N-Functionalized Tertiary Sulfonimidamides.

9. Harnessing Sulfinyl Nitrenes: A Unified One-Pot Synthesis of Sulfoximines and Sulfonimidamides.