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Article Dans Une Revue Angewandte Chemie Année : 2022

Umpolung of Indoles: Triflic Acid-Mediated C3-Regioselective Hydroarylation of N-H Indoles

Résumé

The direct dearomative addition of arenes to the C3-position of unprotected indoles is reported under operationally simple conditions, using triflic acid at room temperature. The present regioselective hydroarylation is a straightforward manner to generate an electrophilic indole at the C3-position without the need of a deactivating acetyl group at the indolic nitrogen as in previously reported strategies. This atom economical method delivers biologically relevant 3-arylindolines and 3,3-spiroindolines in high yields and regioselectivities from both intra-and intermolecular processes. DFT computations suggest the stabilization of cationic or dicationic intermediates with H-bonded (TfOH)n clusters.

Domaines

Chimie organique
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Dates et versions

hal-03769481 , version 1 (05-09-2022)

Identifiants

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Nazarii Sabat, Weiping Zhou, Vincent Gandon, Xavier Guinchard, Guillaume Vincent. Umpolung of Indoles: Triflic Acid-Mediated C3-Regioselective Hydroarylation of N-H Indoles. Angewandte Chemie, 2022, 134 (30), pp.e202204400. ⟨10.1002/ange.202204400⟩. ⟨hal-03769481⟩
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