No abstract

A scalable and operationally simple decarboxylative trifluoromethylation of (hetero)arenes with easily accessible C 6 F 5 I(OCOCF 3 ) 2 under photoredox catalysis has been developed. This method is tolerant of various (hetero)arenes and functional groups. Notably, C 6 F 5 I is recycled from the decarboxylation reaction and further used for the preparation of C 6 F 5 I(OCOCF 3 ) 2 . The combination of photoredox catalysis and hypervalent iodine reagent provides a practical approach for the application of trifluoroacetic acid in trifluoromethylation reactions.

Novel heteroaryl triflones including oxindole, pyrazolone, pyridine, and quinoline derivatives have been regioselectively synthesized by LDA-mediated thia-Fries rearrangement for the first time. These reactions are also the first examples of the application of anionic thia-Fries rearrangement in heteroaromatic compounds.

Pentafluorosulfanyl chloride (SF 5 Cl) is the most prevalent reagent for the incorporation of SF 5 group into organic compounds. However, the preparation of SF 5 Cl often relies on hazardous reagents and specialized apparatus. Herein, we described a safe and practical synthesis of a bench-stable and easy-to-handle solution of SF 5 Cl in nhexane under gas-reagent-free conditions. The synthetic application of SF 5 Cl was demonstrated through the unprecedented reaction with diazo compounds. The chemoselective hydroand chloropentafluorosulfanylations of a-diazo carbonyl compounds were developed in the presence of K 3 PO 4 or copper catalyst, respectively. These reactions provide a direct and efficient access to various a-pentafluorosulfanyl carbonyl compounds of high value for potential applications.Scheme 1. Preparation of a solution of SF 5 Cl in n-hexane.