&#945;-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles.

Caiuby, Clarice A D; de Jesus, Matheus P; Burtoloso, Antonio C B

α-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles.

Caiuby, Clarice A D; de Jesus, Matheus P; Burtoloso, Antonio C B.

Afiliação

Caiuby CAD; Instituto de QuiÌmica de São Carlos, Universidade de São Paulo, CEP, 13560-970 São Carlos, SP, Brazil.
de Jesus MP; Instituto de QuiÌmica de São Carlos, Universidade de São Paulo, CEP, 13560-970 São Carlos, SP, Brazil.
Burtoloso ACB; Instituto de QuiÌmica de São Carlos, Universidade de São Paulo, CEP, 13560-970 São Carlos, SP, Brazil.

J Org Chem ; 85(11): 7433-7445, 2020 Jun 05.

Article em En | MEDLINE | ID: mdl-32342687

RESUMO

Imidoyl sulfoxonium ylides are presented for the first time as potential precursors to generate α-imino metal-carbene intermediates and applied in direct C-H functionalization reactions catalyzed by [Ir(cod)Cl]2 (4 mol %) to provide 2-substituted indoles (up to 70% yield) in just one step. This class of sulfur ylide is successfully obtained from imidoyl chloride and dimethylsulfoxonium methylide (23 new examples in 45-85% yield) or by imino group formation from the corresponding ß-keto sulfoxonium ylides and anilines in the presence of TiCl4 as a Lewis acid (9 examples in 33-94% yield).

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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: J Org Chem Ano de publicação: 2020 Tipo de documento: Article País de afiliação: Brasil País de publicação: Estados Unidos

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