Literature DB >> 25831154

Trifluoromethyl sulfoxides from allylic alcohols and electrophilic SCF3 donor by [2,3]-sigmatropic rearrangement.

Mayaka Maeno1,2, Norio Shibata2, Dominique Cahard1.   

Abstract

An electrophilic trifluoromethylthiolation of allylic alcohols produces the corresponding allylic trifluoromethanesulfenates, which spontaneously rearrange into trifluoromethyl sulfoxides via a [2,3]-sigmatropic rearrangement. The reaction is straightforward and proceeds in good to high yields for the preparation of various allylic trifluoromethyl sulfoxides.

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Year:  2015        PMID: 25831154     DOI: 10.1021/acs.orglett.5b00750

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


  4 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 trifluoromethyl aryl sulfoxides by trifluoromethylthiolation of arenes and subsequent oxidation with hydrogen peroxide.

Authors:  Monika Horvat; Gregor Kodrič; Marjan Jereb; Jernej Iskra
Journal:  RSC Adv       Date:  2020-09-18       Impact factor: 4.036

3.  2-Diazo-1-phenyl-2-((trifluoromethyl)sulfonyl)ethan-1-one: Another Utility for Electrophilic Trifluoromethylthiolation Reactions.

Authors:  Zhongyan Huang; Kenta Okuyama; Chen Wang; Etsuko Tokunaga; Xiaorui Li; Norio Shibata
Journal:  ChemistryOpen       Date:  2016-01-28       Impact factor: 2.911

4.  Synthesis, Characterization, Cytotoxicity, and Antibacterial Properties of trans-γ-Halo-δ-lactones.

Authors:  Angelika Kamizela; Barbara Gawdzik; Mariusz Urbaniak; Łukasz Lechowicz; Agata Białońska; Weronika Gonciarz; Magdalena Chmiela
Journal:  ChemistryOpen       Date:  2018-07-23       Impact factor: 2.911

  4 in total

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