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Article Dans Une Revue Organic Letters Année : 2021

Complementary Site-Selective Sulfonylation of Aromatic Amines by Superacid Activation

Résumé

Under superacidic conditions, aniline and indole derivatives are sulfonylated at low temperature with easy-to-access arenesulfonic acids or arenesulfonyl hydrazides. By modification of the functional-group directing effect through protonation, this method allows nonclassical site functionalization by overcoming the innate regioselectivity of electrophilic aromatic substitution. This superacid-mediated sulfonylation of arenes is complementary to existing methods and can be applied, through protection by protonation, to the late-stage site-selective functionalization of natural alkaloids and active pharmaceutical ingredients.

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Chimie
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Dates et versions

hal-03358394 , version 1 (29-09-2021)

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Paul Bourbon, Emeline Appert, Agnès Martin-Mingot, Bastien Michelet, Sébastien Thibaudeau. Complementary Site-Selective Sulfonylation of Aromatic Amines by Superacid Activation. Organic Letters, 2021, 23 (11), pp.4115-4120. ⟨10.1021/acs.orglett.1c00994⟩. ⟨hal-03358394⟩
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