Regioselective Gold-Catalyzed Hydration of CF₃- and SF₅-alkynes

Abstract

The regioselective gold-catalyzed hydration of CF3- and SF5-alkynes is described. The corresponding trifluoromethylated and pentasulfanylated ketones are obtained in up to 91% yield as single regioisomers showcasing the use of CF3 and SF5 as highly efficient directing groups in this reaction. Notably, this transformation represents the first use of CF3- and SF5-alkynes in gold catalysis.

Multitasking FeOCN Composite as an Economic, Heterogeneous Catalyst for 1‐Octene Hydroformylation and Hydration Reactions

“…A strong absorption band at 1382 cm −1 and a weak absorption band at 2343 cm −1 confirms the presence of Fe 3 C . Absorption bands at 2924 cm −1 and 3440 cm −1 are related to CH stretching and OH . The Raman spectrum of FeOCN composite shows A 1g bands at 219 and 488 cm −1 while E g bands were obtained at 285, 403 and 606 cm −1 .…”

“…[43] A strong absorption band at 1382 cm À 1 and a weak absorption band at 2343 cm À 1 confirms the presence of Fe 3 C. [44] Absorption bands at 2924 cm À 1 and 3440 cm À 1 are related to CH stretching and OH. [45] The Raman spectrum of FeOCN composite shows A 1g bands at 219 and 488 cm À 1 while E g bands were obtained at 285, 403 and 606 cm À 1 . A E u mode band is visible at 658 cm À 1 and a 2E u band is visible at 1314 cm À 1 which represents second order phonon-photon interaction.…”

Chemoselective Hydro(Chloro)pentafluorosulfanylation of Diazo Compounds with Pentafluorosulfanyl Chloride

“…The reactions of SF 5 Cl mainly involve the atom‐transfer radical addition (ATRA) with unsaturated compounds, such as alkenes (Scheme 2 a) [8, 15] and alkynes (Scheme 2 b). [7f, 16] The resulting chloropentafluorosulfanylated products are important precursors for the preparation of other SF 5 ‐containing compounds. The transformation of SF 5 Cl adducts formed from vinyl esters or ethers is the common approach to α‐SF 5 aldehydes, ketones, carboxylic acids, and esters (Scheme 2 c).…”

“… [7a,c, 17] Recently, Paquin developed a multistep synthesis of α‐SF 5 ketones starting from the addition of SF 5 Cl to alkynes (Scheme 2 d). [7f] These α‐SF 5 carbonyl compounds are valuable building block for further diversification [7c,d, 18] . To the best of our knowledge, there was only one example of the direct synthesis of α‐SF 5 carbonyl compounds from the addition of SF 5 Cl to ketene (Scheme 2 e).…”

Chemoselective Hydro(Chloro)pentafluorosulfanylation of Diazo Compounds with Pentafluorosulfanyl Chloride

“…[5] To date, most of these synthetic methods focused on the improvement of the fluorination process for the preparation of SF 5 -substituted aromatic compounds [6] and transformation of SF 5 -containing building blocks. [7] The synthesis of aliphatic pentafluorosulfanylated compounds through direct pentafluorosulfanylation reactions was less developed probably due to a lack of efficient and easily available pentafluorosulfanylating reagents.…”