Superelectrophilic activation in superacid HF/SbF(5) and synthesis of benzofused sultams.
The synthesis of benzofused sultams and/or fluorinated sulfonamides, starting from N-allylic sulfonamides, was performed in superacid HF/SbF(5), through superelectrophilic activation. A dramatic effect of superacid composition on the selectivity of the reaction was shown and applied to the synthesis of cyclic 4-aminobenzenesulfonamides.
Liu
Fei
F
Laboratoire Synthese et Reactivite des Substances Naturelles, UMR 6514, 40, avenue du Recteur Pineau, F-86022, Poitiers Cedex, France.
Martin-Mingot
Agnès
A
Jouannetaud
Marie-Paule
MP
Zunino
Fabien
F
Thibaudeau
Sébastien
S
D000965:Antimony / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D005459:Fluorides / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis / Q000737:chemistry; D006858:Hydrofluoric Acid / Q000737:chemistry; D015394:Molecular Structure; D000077145:Sulfanilamide; D013424:Sulfanilamides / Q000138:chemical synthesis* / Q000737:chemistry
D006845:Hydrocarbons, Fluorinated; D013424:Sulfanilamides; D000077145:Sulfanilamide; C529140:antimony pentafluoride; D000965:Antimony; D005459:Fluorides; D006858:Hydrofluoric Acid