1-Butyl-3-methylimidazolium p-toluenesulfinate: a novel reagent for synthesis of sulfones and β-ketosulfones in ionic liquid

Ligand-Mediated and Copper-Catalyzed C(sp3)-H Bond Functionalization of Aryl Ketones with Sodium Sulfinates under Mild Conditions

“…β -Keto sulfones are of much significant intermediates owing to their ubiquitous presence and versatile applications in biological and pharmaceutical areas 11 12 , as well as in the synthesis of acetylenes 13 , olefins 14 , allenes 15 , vinyl sulfones 16 , and some natural products 17 . As a result of their synthetic value and versatile reactivity, great efforts have been made towards constructing β -keto sulfones during the past decades 18 19 20 21 22 23 24 .…”

Enantioselective Sulfonation of Enones with Sulfonyl Imines by Cooperative N‐Heterocyclic‐Carbene/Thiourea/Tertiary‐Amine Multicatalysis

“…Instead, electrostatic interactions between the negatively charged sulfinic anion and the positively charged triazolium NHC precatalyst [14] also played a role in the asymmetric induction. For example, with the thiourea cocatalyst These results suggested that the nucleophilic sulfinic anion was not delivered to enones as an isolated species.…”

“…For example, with the thiourea cocatalyst These results suggested that the nucleophilic sulfinic anion was not delivered to enones as an isolated species. Chalcone-type enones with different aromatic substituents reacted smoothly to afford the corresponding g-ketosulfones in good yields with excellent enantioselectivity ( Table 2, entries [1][2][3][4][5][6][7][8][9][10][11][12][13][14]. We next examined the scope of the reaction under the optimized conditions (Table 2).…”

Enantioselective Sulfonation of Enones with Sulfonyl Imines by Cooperative N‐Heterocyclic‐Carbene/Thiourea/Tertiary‐Amine Multicatalysis

“…For example, with the thiourea cocatalyst A2, B5 (10 mol %), 0 8C, 72 h [d] 67 96: 4 12 ent-A2, [e] B5 (10 mol %), 0 8C, 72 h [d] These results suggested that the nucleophilic sulfinic anion was not delivered to enones as an isolated species. Instead, electrostatic interactions between the negatively charged sulfinic anion and the positively charged triazolium NHC precatalyst [14] also played a role in the asymmetric induction. We next examined the scope of the reaction under the optimized conditions (Table 2).…”