Literature DB >> 21235264

Synthesis of CF3-substituted sulfoximines from sulfonimidoyl fluorides.

Rafal Kowalczyk1, Andrew J F Edmunds, Roger G Hall, Carsten Bolm.   

Abstract

N-Protected trifluoromethyl-substituted sulfoximines have been prepared by treatment of sulfonimidoyl fluorides with a combination of the Ruppert-Prakash reagent (TMSCF(3)) and tetrabutyl ammonium fluoride (TBAF). The starting materials were accessed following two synthetic routes, and for each reaction sequence the substrate scope was evaluated. Accordingly, a wide variety of aryl-substituted products were obtained in moderate to good yield.

Entities:  

Year:  2011        PMID: 21235264     DOI: 10.1021/ol103030w

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


  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.  One-Pot Synthesis of N-Iodo Sulfoximines from Sulfides.

Authors:  Anže Zupanc; Marjan Jereb
Journal:  J Org Chem       Date:  2021-03-25       Impact factor: 4.354

3.  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

4.  Modern Stereoselective Synthesis of Chiral Sulfinyl Compounds.

Authors:  Elżbieta Wojaczyńska; Jacek Wojaczyński
Journal:  Chem Rev       Date:  2020-04-29       Impact factor: 60.622

Review 5.  (Hetero)aryl-SVI Fluorides: Synthetic Development and Opportunities.

Authors:  Marc Magre; Shengyang Ni; Josep Cornella
Journal:  Angew Chem Int Ed Engl       Date:  2022-04-27       Impact factor: 16.823

6.  Metal-free electrochemical fluorodecarboxylation of aryloxyacetic acids to fluoromethyl aryl ethers.

Authors:  Michael Berger; John D Herszman; Yuji Kurimoto; Goswinus H M de Kruijff; Aaron Schüll; Sven Ruf; Siegfried R Waldvogel
Journal:  Chem Sci       Date:  2020-06-01       Impact factor: 9.825

7.  Sulfinamide Synthesis Using Organometallic Reagents, DABSO, and Amines.

Authors:  Pui Kin Tony Lo; Gwyndaf A Oliver; Michael C Willis
Journal:  J Org Chem       Date:  2020-04-14       Impact factor: 4.354

8.  Silicon-Free SuFEx Reactions of Sulfonimidoyl Fluorides: Scope, Enantioselectivity, and Mechanism.

Authors:  Dong-Dong Liang; Dieuwertje E Streefkerk; Daan Jordaan; Jorden Wagemakers; Jacob Baggerman; Han Zuilhof
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-11       Impact factor: 15.336

9.  Anion-Initiated Trifluoromethylation by TMSCF3: Deconvolution of the Siliconate-Carbanion Dichotomy by Stopped-Flow NMR/IR.

Authors:  Craig P Johnston; Thomas H West; Ruth E Dooley; Marc Reid; Ariana B Jones; Edward J King; Andrew G Leach; Guy C Lloyd-Jones
Journal:  J Am Chem Soc       Date:  2018-08-21       Impact factor: 15.419

  9 in total

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