Harnessing the catalytic behaviour of 1, 1, 1, 3, 3, 3-hexafluoro-2-propanol (HFIP): An expeditious synthesis of thioesters. Issue 19 (10th May 2017)

• Record Type: Journal Article
• Authors: Singh, Pallavi; Peddinti, Rama Krishna
• Is Part Of: Tetrahedron letters. Volume 58:Issue 19(2017)
• Page Start: 1875
• Page End: 1878
• Publication Date: 2017-05-10
• Subjects: HFIP catalysis -- Metal-free -- Base-free -- Acid-free -- High atom economy; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.04.004
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Acid-, base- and metal-free and expeditious synthesis of thioesters is unravelled. Novel HFIP-catalyzed synthesis of thioesters in excellent yields is reported. Proceeds under aerobic conditions at room temperature with wide substrate scope. No additional reagent/solvent, no workup required in this clean method. Reuse of HFIP, high atom economy, gram-scale synthesis are noteworthy. Abstract: A novel, efficient, metal-, base- and acid-free straightforward protocol has been developed for the construction of useful thioesters. The immense catalytic potential of HFIP for promoting the thiocarbonylation of acyl halides and thiols is disclosed. HFIP was recovered with ease and reused for further reactions without any loss of reactivity. Both aryl and alkyl thiols bearing electron-donating and electron-withdrawing groups as well as aryl- and alkyl acyl halides worked well in this reaction. Inexpensive precursors, short reaction time, obviating workup, high atom economy, and gram-scale preparation are the significant features of the developed eco-friendly route for S-carbonylation of thiols.