2262-07-9Relevant articles and documents
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Hine,Ghirardelli
, p. 1550 (1958)
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Synthesis of aryl 2,2,2-trifluoroethyl sulfides
Menczinger, Bálint,Nemes, Anikó,Szabó, Dénes,Schlosser, Gitta,Jernei, Tamás,Csámpai, Antal,Rábai, József
, (2020/01/28)
Aryl 2,2,2-trifluoroethyl sulfides were synthesized by copper(I)-catalyzed nucleophilic aromatic substitution reaction (Goldberg-Ullmann coupling). The method requires aryl iodides and 2,2,2-trifluoroethyl thioacetate as starting materials, benzylamine as solvent and base, and copper(I) bromide as a catalyst. The reaction mixture was stirred at 110 °C for 6 h under inert atmosphere to afford the targeted aryl 2,2,2-trifluoroethyl sulfides in moderate to good yield.
New sulfuryl fluoride-derived alkylating reagents for the 1,1-dihydrofluoroalkylation of thiols
Foth, Paul J.,Gu, Frances,Bolduc, Trevor G.,Kanani, Sahil S.,Sammis, Glenn M.
, p. 10331 - 10335 (2019/11/20)
Herein, we report a new method for the one-pot synthesis of 1,1-dihydrofluoroalkyl sulfides by bubbling sulfuryl fluoride (SO2F2) through a solution of the corresponding alcohol and thiol. The reaction proceeds through a new class of bis(1,1-dihydrofluoroalkyl) sulfate reagents, to afford the desired 1,1-dihydrofluoroalkyl sulfides in 55-90% isolated yields. The bis(1,1-dihydrofluoroalkyl) sulfates are highly chemoselective for thiol alkylation, and are unreactive with competing, unprotected nucleophiles, including amines, alcohols, and carboxylic acids.
Dealkylative intercepted rearrangement reactions of sulfur ylides
Empel, Claire,Hock, Katharina J.,Koenigs, Rene M.
supporting information, p. 338 - 341 (2019/01/09)
Sulfur ylides are well-known to undergo sigmatropic rearrangement reaction. Herein, we describe a novel reactivity of sulfur ylides, which provides access to the product of a formal functional group metathesis upon dealkylative interception of the rearrangement process. Using a simple iron catalyst and in situ generated diazoalkanes this method provides access to α-mercaptoacetonitrile derivatives.