Efficient synthesis of 5′-fluoroalkoxythiazoles via α-bromo-α-fluoroalkoxyacetophenones Hantzsch type cyclization with thioureas or thioamides

Advances in the Synthesis and Application of Tetrafluoroethylene‐ and 1,1,2,2‐Tetrafluoroethyl‐Containing Compounds

“…Base‐catalyzed addition of alcohols and phenols to TFE leads to the formation of 1,1,2,2‐tetrafluoroethyl ethers 18 (Table ) , , . Even though the reaction is usually performed under elevated temperature and pressure, Sokolenko and co‐workers described the product formation even at ambient pressure (Table , entries 7 and 8) , . In polyols, all hydroxyls participate in the TFE addition (Table , entries 10–13) , .…”

“…In polyols, all hydroxyls participate in the TFE addition (Table , entries 10–13) , . Products from entries 7 and 8 serve as precursors for the synthesis of various heterocyclic compounds with the 1,1,2,2‐tetrafluoroethoxy group attached directly to the heterocycle ring , , …”

Synthetic Approaches to Trifluoromethoxy‐Substituted Compounds

“…The formation of this unstable anion from TFMT in the presence of fluoride sources at low temperature (−30 °C) has also been exploited . Whereas several trifluoromethanolate salts have been isolated (Scheme a),– the trifluoromethoxide anion (from silver and tetrabutylammonium trifluoromethoxide) can also be generated in situ (Scheme b) . Both methods have enabled the trifluoromethoxylation of alkyl halides or pseudohalides (I, Br, OTf), especially for primary or activated secondary starting materials; however, almost no reactivity was observed with unactivated secondary as well as tertiary alkyl halides.…”

Selective C–O bond formation via a photocatalytic radical coupling strategy: access to perfluoroalkoxylated (ORF) arenes and heteroarenes

“…2 , 26 Umemoto et al addressed this issue with an elegant electrophilic O–R F bond formation strategy via radical intermediates, 20 yet the non-selective formation of O - and C -perfluoroalkylated products limited its synthetic utility. Although new strategies for the synthesis of perfluoroalkoxylated (hetero)arenes have emerged over the past few years, 23 , 27 – 32 a general and mild catalytic process has yet to be developed. As a result, the full potential of perfluoroalkoxylated (hetero)aromatic compounds has not been fully exploited across a broad spectrum of technological applications.…”