Electrochemical bromocyclization enables 3,5-diversification of heterocyclic indolines

Ren, Hai; Wang, Rui-An; Shi, Jun; Song, Jun-Rong; Wu, Wei; Chi, Qin; Zhang, Ni

doi:10.1039/d3ob00985h

Org. Biomol. Chem.

2023

DOI: 10.1039/d3ob00985h

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Electrochemical bromocyclization enables 3,5-diversification of heterocyclic indolines

Hai Ren,

Rui-An Wang,

Jun Shi

et al.

Abstract: We report a protonic-acid-promoted electrosynthetic strategy for the dearomative dibromocyclization of tryptamine/tryptophol derivatives for the convenient late-stage 3,5-diversification of heterocyclic indolines.

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2024

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Cited by 2 publications

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Electrochemically Promoted Skeleton Transformation of 2,1‐Benzisoxazoles to Alkyl Sulfones

Wu,

Ren,

Zhu

et al. 2024

Adv Synth Catal

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Abstract. This study developed an electrochemically promoted skeleton transformation reaction of 2,1‐benzisoxazoles to synthesize alkyl sulfones. The synthesis of alkyl sulfone products in 68%‐93% yields by using 2,1‐benzisoxazole and sulfonate as substrates, and acetonitrile and water were employed as solvents. Mechanism study shows that this reaction work involving the ring opening, the removal of the oxygen atom of 2,1‐benzisoxazoles, and the formation of C(sp3)‐sulfonylation under electrochemical conditions.

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Electrochemically Promoted Skeleton Transformation of 2,1‐Benzisoxazoles to Alkyl Sulfones

Wu,

Ren,

Zhu

et al. 2024

Adv Synth Catal

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Synthesis of indolyl pyrroloindolines via a cascade arylation/cyclization of indole acetamides with 3-substituted indoles

Zhang,

Han,

Zhang

et al. 2024

Org. Chem. Front.

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Electrochemical bromocyclization enables 3,5-diversification of heterocyclic indolines

Abstract: We report a protonic-acid-promoted electrosynthetic strategy for the dearomative dibromocyclization of tryptamine/tryptophol derivatives for the convenient late-stage 3,5-diversification of heterocyclic indolines.

Cited by 2 publications

References 46 publications

Electrochemically Promoted Skeleton Transformation of 2,1‐Benzisoxazoles to Alkyl Sulfones

Electrochemically Promoted Skeleton Transformation of 2,1‐Benzisoxazoles to Alkyl Sulfones

Synthesis of indolyl pyrroloindolines via a cascade arylation/cyclization of indole acetamides with 3-substituted indoles

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