Reactions of 4-substituted tetrafluoropyridine derivatives with sulfur nucleophiles: SNAr and annelation processes

Reactions of sulfur centred nucleophiles with tetrafluoropyridine derivatives gave substitution or ring-fused products arising from displacement of the 4-substituent or ring fluorine. [Display omitted] ► 4-Tetrafluoropyridine derivatives react with sulfur nucleophiles. ► Ipso substitution of 4-nitro...

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Bibliographic Details
Published in:Journal of fluorine chemistry 2012-11, Vol.143, p.148-154
Main Authors: Fox, Mark A., Sandford, Graham, Slater, Rachel, Yufit, Dmitrii S., Howard, Judith A.K., Vong, Antonio
Format: Article
Language:English
Subjects:
Nucleophilic aromatic substitution
Perfluoroaromatic
Perfluoroheterocyclic
Tetrafluoropyridine
Thieno[2,3-c]pyridine
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Summary:Reactions of sulfur centred nucleophiles with tetrafluoropyridine derivatives gave substitution or ring-fused products arising from displacement of the 4-substituent or ring fluorine. [Display omitted] ► 4-Tetrafluoropyridine derivatives react with sulfur nucleophiles. ► Ipso substitution of 4-nitro and 4-phenylsulfonyl substituents occur. ► Thieno[2,3-c]pyridine products formed from 4-cyano-tetrafluoropyridine. Reactions of model sulfur centred nucleophiles with 4-nitro-, 4-phenylsulfonyl- and 4-cyano-tetrafluoropyridine gave products arising from substitution of the nitro- and sulfonyl substituent or ring fluorine respectively. Ring fused products are formed upon reaction of 4-cyano-tetrafluoropyridine with mercapto-acetic acid ethyl ester.
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2012.05.011