Synthesis of trifluoromethylated 2H-azirines through Togni reagent-mediated trifluoromethylation followed by PhIO-mediated azirination

• Jiyun Sun,
• Xiaohua Zhen,
• Huaibin Ge,
• Guangtao Zhang,
• Xuechan An and
• Yunfei Du

Beilstein J. Org. Chem. 2018, 14, 1452–1458, doi:10.3762/bjoc.14.123

• CF3 group into various organic molecules, the further development of novel routes for the selective trifluoromethylation is of continuing interest for synthetic and medicinal chemists. Togni reagents, including 1-(trifluoromethyl)-1,2-benziodoxol-3(1H)-one (1) and trifluoromethyl-1,3-dihydro-3,3

• chemistry [24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40]. For example, the Togni reagents have been successfully applied to introduce the CF3 group into pharmaceutical agents such as the fluoxetine derivative D (Figure 1), the mefloquine derivative E [41] and compound F [42] – a

• is well documented that Togni reagents can realize the direct trifluoromethylation of alkenes [58][59][60] and electron-rich enamides [61]. Inspired by this, we envisaged that Togni reagent 1 could also enable the introduction of a CF3 group to the β-position of enamine substrates, and the so

One-pot three-component route for the synthesis of S-trifluoromethyl dithiocarbamates using Togni’s reagent

• Azim Ziyaei Halimehjani,
• Martin Dračínský and
• Petr Beier

Beilstein J. Org. Chem. 2017, 13, 2502–2508, doi:10.3762/bjoc.13.247

• rotation are in reasonable agreement with the experiments. Keywords: dithiocarbamates; electrophilic trifluoromethylation; Togni reagents; Introduction Dithiocarbamates are well known for their manifold applications as pesticides, fungicides and crop protection agents in agriculture [1][2][3], as

Shelf-stable electrophilic trifluoromethylating reagents: A brief historical perspective

• Norio Shibata,
• Andrej Matsnev and
• Dominique Cahard

Beilstein J. Org. Chem. 2010, 6, No. 65, doi:10.3762/bjoc.6.65

• reagent 16 and much higher yields than the commercially available Umemoto or Togni reagents in trifluoromethylation reactions. Of particular interest, the vinylogous trifluoromethylation of dicyanoalkylidenes afforded an access to allylic trifluoromethylated compounds (Scheme 13). All the reactions were

• triflates. One-pot synthesis of Umemoto’s type reagents. Preparation of sulfonium salts by transformation of CF3− into CF3+. Selected reactions with the new Yagupolskii reagents. Synthesis of heteroaryl-substituted sulfonium salts. First neutral S-CF3 reagents. Synthesis of Togni reagents. aYield for the