Fluorination of highly basic (hetero)aryl and alkenyl lithiums is crucial in the chemical industry but the current fluorinating agents have significant drawbacks. We will report the high-yield synthesis of N-fluoro-N-(tert-butyl)-tert-butanesulfonamide (NFBB) and its reaction with a wide range of (hetero)aryl and alkenyl lithium species to produce the corresponding (hetero)aryl and alkenyl fluorides in unprecedented high yields. We will also report a user-friendly, thermally stable, and reactive trifluoromethoxylating reagent, trifluoromethyl nonaflate (TFNf). TFNf permits the regio- and stereoselective hydro(halo)trifluoro methoxylation of alkyne derivatives. As of late, the introduction of CF3S and CF3Se into organic molecules has garnered interest due to their acquired high Hansch lipophilicity parameters and strong electron-withdrawing effects, but the synthetic methodologies for introducing these groups are in their infancy. We will describe the first gold-catalyzed C−SCF3/SeCF3 cross-coupling reaction using gold redox catalysis [(MeDalphos)AuCl], AgSCF3 or Me4NSeCF3, and organohalides as substrates. This protocol facilitates an efficient one-stop shop synthesis of aryl/alkenyl/alkynyl trifluoromethylthio- and selenoethers with a broad substrate scope and excellent yields.

Fluorination of lithiated species and one stop-shop syntheses of S, O, and Se-trifluoromethylated compounds

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ACS Fall 2022

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