Hafnium trifluoromethanesulfonate (hafnium triflate) as a highly efficient catalyst for chemoselective thioacetalization and transthioacetalization of carbonyl compounds.
A range of carbonyl compounds including aliphatic and aromatic aldehydes and ketones were converted to the corresponding thioacetals in high yields in the presence of a catalytic amount of hafnium trifluoromethanesulfonate (0.1 mol %, room temperature). The mild conditions tolerated various sensitive functional and protecting groups and were racemization-free when applied to alpha-aminoaldehydes. Transacetalization and chemoselective thioacetalization of aromatic aldehydes in the presence of aliphatic aldehydes and ketones were also documented.
Wu
Yan-Chao
YC
Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France.
Zhu
Jieping
J
D000080:Acetals / Q000737:chemistry*; D000447:Aldehydes; D000838:Anions; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D006195:Hafnium / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D007659:Ketones; D008956:Models, Chemical; D012997:Solvents; D013438:Sulfhydryl Compounds; D013457:Sulfur Compounds / Q000737:chemistry*
D000080:Acetals; D000447:Aldehydes; D000838:Anions; D006845:Hydrocarbons, Fluorinated; D007659:Ketones; D012997:Solvents; D013438:Sulfhydryl Compounds; D013457:Sulfur Compounds; D002244:Carbon; D006195:Hafnium