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Superelectrophilic activation in superacid HF/SbF(5) and synthesis of benzofused sultams.

Organic letters (2010-01-19)
Fei Liu, Agnès Martin-Mingot, Marie-Paule Jouannetaud, Fabien Zunino, Sébastien Thibaudeau
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Supelco
Sulfanilamide melting point standard, Pharmaceutical Secondary Standard; Certified Reference Material
Sigma-Aldrich
Sulfanilamide, puriss. p.a., ≥99% (calc. to the dried substance)
Supelco
Sulfanilamide, VETRANAL®, analytical standard
Sigma-Aldrich
Sulfanilamide, ≥98%
Sigma-Aldrich
Sulfanilamide, Vetec, reagent grade, 97%