Na 2 S·9H 2 O Enabled Defluorodisulfuration and Hydrodefluorination of Perfluorobutyl Tetralones: Synthesis of Trifluoromethyl 1,2-Dithioles.

Autor: Yu ZL; Technical Institute of Fluorochemistry, Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China., Feng MH; Technical Institute of Fluorochemistry, Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China., Zhang PY; Technical Institute of Fluorochemistry, Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China., Xu H; Technical Institute of Fluorochemistry, Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China., Ge D; Technical Institute of Fluorochemistry, Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China., Ma M; Department of Chemistry and Materials Science, College of Science, Nanjing Forestry University, Nanjing 210037, China., Shen ZL; Technical Institute of Fluorochemistry, Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China., Chu XQ; Technical Institute of Fluorochemistry, Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2023 Jun 16; Vol. 25 (23), pp. 4388-4393. Date of Electronic Publication: 2023 Jun 02.
DOI: 10.1021/acs.orglett.3c01573
Abstrakt: An unprecedented defluorocyclization of perfluorobutyl tetralones with Na 2 S·9H 2 O was developed for the synthesis of trifluoromethyl 1,2-dithioles, which provided chemists novel access to biologically and pharmaceutically relevant organofluorides. Successive C(sp 3 )-F bond functionalization at the perfluoroalkyl chain is vital for the formation of four C-H/C-S/S-S bonds and a five-membered S-heterocycle assembly. Cheap, weakly toxic, and odorless inorganic sulfide Na 2 S·9H 2 O acts as both a disulfurating precursor and a hydrodefluorinating reagent in this tandem multi-bond-interconverting reaction.
Databáze: MEDLINE