Electrosynthesis of β-trifluoromethylated O,S-acetal and α-(trifluoromethyl)acrylate derivatives from 2-ethoxycarbonyl-3,3,3-trifluoropropyl phenyl sulfide using a fluoride ion mediator

RCM-Mediated Synthesis of Trifluoromethyl-Containing Nitrogen Heterocycles

“…In addition, the corresponding alcohol, 2-trifluoromethyl-2-propenol, is not trivial to make. For example, straightforward reduction of the corresponding carboxylic acid, 2-trifluoromethylacrylic acid, either direct via LiAlH 4 reduction or indirect via acid chloride formation followed by LiAlH 4 reduction appeared in our hands to be either unreliable or laborious, so that we decided to develop a novel pathway for its synthesis (Scheme ). Since the reported problems were generally associated with the reactivity of the α,β-unsaturated acrylic system, we envisaged that it would be advantageous to protect the olefin in some way.…”

Fluorine-containing alkyl(aryl) vinyl sulfides

“…3 HF in acetonitrile results in b-phenylthio-a-(trifluoromethyl)acrylate 1. 30 Presumably, this reaction proceeds via a radical cation, which reacts with the fluoride ion. The b-fluorinated sulfide formed in the first step is unstable under the reaction conditions and is readily dehydrofluorinated to give sulfide 1.…”

Base-Induced Decarboxylative 1,1-Alkoxy Thiolation via Hydrothiolation of Vinylene Carbonate

“…However, such functionalizations revolve mostly around 1,2-additions under thermal, photochemical, or electrochemical conditions involving ionic or radical pathways (Figure a) . On the other hand, despite being synthetically more useful, 1,1-difunctionalization is mostly limited to terminal olefins under metal catalysis . Organosulfur compounds are found in numerous drugs, natural products, and functional materials .…”