Oxidative decarboxylation/trifluoromethylselenolation
of primary,
secondary, and tertiary aliphatic carboxylic acids with the nucleophilic
[Me4N][SeCF3] salt and an organic photocatalyst
is described. The reaction proceeds smoothly at room temperature under
transition-metal-free conditions and affords the corresponding trifluoromethylselenolated
products in good yields. Advantages of the method include good functional
group tolerance, without preactivation of the acids, and late-stage
functionalization of the complex drug molecules. This protocol represents
the first decarboxylative trifluoromethylselenolation of carboxylic
acids to trifluoromethyl selenoethers.
The first oxidative trifluoromethylselenolation of nucleophilic (hetero)arenes with the nucleophilic [Me4N][SeCF3] salt under transition-metal-free conditions is described.
An efficient and transition-metal-free
method for the synthesis
of the structurally diversified trifluoroethylthiol phenanthridines
and 3,4-dihydroisoquinolines is described. Various 2-isothiocyanobiaryls
and aryl alkyl isothiocyanates reacted with phenyl(2,2,2-trifluoroethyl)iodonium
triflate in CH2Cl2 in the presence of trifluoromethanesulfonic
acid at 40 °C to form the corresponding trifluoroethylation/cyclization
products in good to quantitative yields. This work represents the
first construction of trifluoroethylthiol phenanthridine and isoquinoline
derivatives from isothiocyanates in the absence of transition-metal
catalysts by a one-pot procedure.
Highly electrophilic aryl(2,2,2-trifluoroethyl)iodonium triflates have been used for the first time as trifluoroethyl and aryl transfer reagents in Pd-catalyzed functionalization of arylboronic acids. Electron-rich arylboronic acids reacted with aryl(2,2,2-trifluoroethyl)iodonium triflates (2a-b) in CH3CN in the presence of Pd2(dba)3 and K3PO4 at room temperature to provide trifluoroethyl arenes in up to 82% yield, while the reactions of both electron-rich and -poor arylboronic acids with 2a-b in DMF in the presence of Pd[P(t-Bu)3]2 and Cs2CO3 at 40 °C afforded arylation products in up to 99% yield. This tunable protocol allows access to trifluoroethyl arenes or biaryls in good to excellent yields under mild conditions and without the addition of extra ligands.
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