Trifluoromethylthiolation of Unsymmetrical λ3-Iodane Derivatives: Additive-Free, Selective and Scalable Introduction of the SCF3 Group
The reaction of copper trifluoromethyl sulfide with diaryliodonium salts provides a straightforward pathway for the synthesis of aryl trifluoromethyl thioethers under mild reaction conditions and within short reaction times. High chemoselectivity was achieved by using mesityl as a leaving group. A large range of novel [(het)aryl](mesityl)iodonium salts underwent this reaction under the optimized conditions to give the desired products in moderate to good yields.
Nikolaienko, Pavlo,Yildiz, Tülay,Rueping, Magnus
supporting information
p. 1091 - 1094
(2016/03/05)
Trifluoromethylthiolation of diazo compounds through copper carbene migratory insertion
A strategy to introduce the SCF3 group through the Cu I-promoted reaction of diazo compounds with the nucleophilic AgSCF3 trifluoromethylthiolation reagent was developed. Various diazo compounds were smoothly converted under mild conditions to form the C(sp 3)-SCF3 bond. Mechanistically, migratory insertion of SCF3-bearing Cu carbene intermediates is involved in this transformation. Copyright
Direct trifluoromethylthiolation of alcohols under mild reaction conditions: Conversion of R-OH into R-SCF3
A direct process for the trifluoromethylthiolation of allylic and benzylic alcohols under mild conditions has been developed. A wide range of free alcohols underwent nucleophilic substitution in the presence of stable CuSCF3 and BF3·Et2O to give the corresponding products in good to excellent yields.
Nikolaienko, Pavlo,Pluta, Roman,Rueping, Magnus
supporting information
p. 9867 - 9870
(2014/08/18)
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