Literature DB >> 26057854

Silver-Mediated N-Trifluoromethylation of Sulfoximines.

Fan Teng, Jiang Cheng1, Carsten Bolm1.   

Abstract

An unprecedented approach to N-trifluoromethylations of electron-rich nucleophilic sites following a radical pathway is reported. Accordingly, various sulfoximines (19 examples) have been N-trifluoromethylated, providing previously unreported products with satisfying functionality tolerance in moderate to good yields. With a C-N bond length at the N-CF3 moiety of 1.341 Å the respective linkage is shorter than a traditional C-N single bond and comparable with that of a C-N double bond.

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Year:  2015        PMID: 26057854     DOI: 10.1021/acs.orglett.5b01537

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


  7 in total

1.  N-Trifluoromethylthiolated Sulfonimidamides and Sulfoximines: Anti-microbial, Anti-mycobacterial, and Cytotoxic Activity.

Authors:  Niranjan Thota; Parameshwar Makam; Kamal K Rajbongshi; Savania Nagiah; Naeem Sheik Abdul; Anil A Chuturgoon; Amit Kaushik; Gyanu Lamichhane; Anou M Somboro; Hendrik G Kruger; Thavendran Govender; Tricia Naicker; Per I Arvidsson
Journal:  ACS Med Chem Lett       Date:  2019-09-11       Impact factor: 4.345

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.  Efficient Synthesis of Trifluoromethyl Amines through a Formal Umpolung Strategy from the Bench-Stable Precursor (Me4 N)SCF3.

Authors:  Thomas Scattolin; Kristina Deckers; Franziska Schoenebeck
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-09       Impact factor: 15.336

4.  Accessing Perfluoroaryl Sulfonimidamides and Sulfoximines via Photogenerated Perfluoroaryl Nitrenes: Synthesis and Application as a Chiral Auxiliary.

Authors:  Giampiero Proietti; Julius Kuzmin; Azamat Z Temerdashev; Peter Dinér
Journal:  J Org Chem       Date:  2021-11-12       Impact factor: 4.354

5.  Transfer of Electrophilic NH Using Convenient Sources of Ammonia: Direct Synthesis of NH Sulfoximines from Sulfoxides.

Authors:  Marina Zenzola; Robert Doran; Leonardo Degennaro; Renzo Luisi; James A Bull
Journal:  Angew Chem Int Ed Engl       Date:  2016-04-29       Impact factor: 15.336

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

Authors:  Flavia Izzo; Martina Schäfer; Philip Lienau; Ursula Ganzer; Robert Stockman; Ulrich Lücking
Journal:  Chemistry       Date:  2018-06-19       Impact factor: 5.236

7.  Synthesis of Fluorinated Amide Derivatives via a Radical N-Perfluoroalkylation-Defluorination Pathway.

Authors:  Zhiyao Zheng; Angela van der Werf; Marie Deliaval; Nicklas Selander
Journal:  Org Lett       Date:  2020-03-25       Impact factor: 6.005

  7 in total

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