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- W2131871318 abstract "The electrophilic aromatic ring trifluoromethylthiolation of various substituted phenols was accomplished using PhNHSCF3 (N-trifluoromethylsulfanyl)aniline, (1) in the presence of BF3·Et2O (2) or triflic acid as the promoter. The functionalization was exclusively para-selective; phenols unsubstituted in both the ortho- and para positions solely gave the para-substituted SCF3-products in all cases, while para-substituted phenols gave the ortho-substituted SCF3-products. 3,4-Dialkyl substituted phenols yielded the corresponding products according to the Mills-Nixon effect, and estrone and estradiol furnished biologically interesting SCF3-analogues. The highly reactive catechol and pyrogallol substrates gave the expected products smoothly in the presence of BF3·Et2O, whereas less reactive phenols required triflic acid. 2-Allylphenol gave the expected p-SCF3 analogue, which underwent an addition/cyclization sequence and furnished a new di-trifluoromethylthio substituted 2,3-dihydrobenzofuran derivative. Some additional transformations of 4-(trifluoromethylthio)phenol with NBS, NIS, HNO3, HNO3/H2SO4 and 4-bromobenzyl bromide were performed giving bromo-, iodo-, nitro- and benzyl substituted products. The latter derivative underwent Suzuki-Miyaura coupling with phenylboronic acid." @default.
- W2131871318 created "2016-06-24" @default.
- W2131871318 creator A5006174626 @default.
- W2131871318 creator A5027278532 @default.
- W2131871318 date "2015-01-01" @default.
- W2131871318 modified "2023-10-13" @default.
- W2131871318 title "Acid-promoted direct electrophilic trifluoromethylthiolation of phenols" @default.
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- W2131871318 doi "https://doi.org/10.1039/c4ob02633k" @default.
- W2131871318 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/25627036" @default.
- W2131871318 hasPublicationYear "2015" @default.
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