Solvent-controlled switchable multicomponent tandem oxidative triple functionalization of indolines

Zhang, Xiaoxiang; Gu, Xiaoting; Zhang, Yingying; Liao, Junqiu; Xu, Meilan; Zhang, Zhuan; Liang, Taoyuan

doi:10.1039/d4qo00030g

Org. Chem. Front.

2024

DOI: 10.1039/d4qo00030g

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Solvent-controlled switchable multicomponent tandem oxidative triple functionalization of indolines

Xiaoxiang Zhang,

Xiaoting Gu,

Yingying Zhang

et al.

Abstract: A new one-pot method for solvent-controlled switchable tandem oxidative triple functionalization of indolines has been developed via a successive regioselective chalcogenation, oxidation, amination and halogenation, in which iodine serve as...

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Cited by 2 publications

References 94 publications

(21 reference statements)

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Organoselenium-Catalyzed C2,3-Diarylation of N–H Indoles

Zhang,

Liao

et al. 2024

J. Org. Chem.

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An organoselenium-catalyzed C2,3-diarylation of unprotected N−H indoles with electron-rich aromatics has been developed. This one-pot multicomponent tandem cross-dehydrogenation coupling reaction allows for the incorporation of two different aromatic groups to indoles. More importantly, this approach offers significant advantages, including a high atom and step economy, eliminating the need for prepreparation of the reaction substrates, streamlining the synthetic process and enhancing its practicality. Overall, this organoselenium-catalyzed C2,3-diarylation reaction presents an efficient and versatile strategy for the functionalization of indole derivatives.

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Organoselenium-Catalyzed C2,3-Diarylation of N–H Indoles

Zhang,

Liao

et al. 2024

J. Org. Chem.

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Iron-Catalyzed Friedel–Crafts-type 3,5-Diacylation of Indoles

Gu,

Dai,

Qing

et al. 2024

J. Org. Chem.

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The exploration of remote functionalization of indoles is impeded by the inherently dominant reactivity intrinsic to the pyrrole moiety. Herein, we delineate a novel strategy facilitated by Lewis acid mediation, enabling the remote C−H functionalization, which culminates in the synthesis of an array of selectively functionalized indole derivatives, encompassing 3trifluoroacetyl and 5-benzoyl motifs, utilizing trifluoroacetic anhydride and various acyl chlorides. Notably, the protocol exhibits versatility, as epitomized by the extension of C5-acylation to alkylation and sulfonation reactions. This methodology is distinguished by its exemplary regio-and chemo-selectivity, extensive substrate scope, commendable tolerance to a diverse array of functional groups, and the employment of comparatively mild reaction conditions.

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Solvent-controlled switchable multicomponent tandem oxidative triple functionalization of indolines

Abstract: A new one-pot method for solvent-controlled switchable tandem oxidative triple functionalization of indolines has been developed via a successive regioselective chalcogenation, oxidation, amination and halogenation, in which iodine serve as...

Cited by 2 publications

References 94 publications

Organoselenium-Catalyzed C2,3-Diarylation of N–H Indoles

Organoselenium-Catalyzed C2,3-Diarylation of N–H Indoles

Iron-Catalyzed Friedel–Crafts-type 3,5-Diacylation of Indoles

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