A transition-metal-free, base-promoted annulation/ring-cleavage/ring-reconstruction cascade reaction: a facile access to N-protection free indole-indenones

文献情報

出版日 2021-10-05

DOI 10.1039/D1QO01280K

インパクトファクター 5.281

著者

Na Luo, Zhen-Wei Sun, Xing-Xin Xu, Xiao-Qiang Hu, Feng-Cheng Jia

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要旨

A one-step, transition-metal-free, base-promoted cascade reaction of 2-halogenated arylglyoxals with 2-oxindoles is reported herein, which provides a straightforward approach to structurally diverse N-protection free indole-indenones in satisfactory yields. Control experiments indicated that the geminal bisindolin-2-one intermediate played a crucial role in the downstream annulation/ring-cleavage/ring-reconstruction reaction sequence. This novel reaction not only further enriches the reactivity of indolin-2-ones as the recursive enolate anion source, but also achieves thermal-induced α-arylation of oxindoles without a transition-metal catalyst.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

A transition-metal-free, base-promoted annulation/ring-cleavage/ring-reconstruction cascade reaction: a facile access to N-protection free indole-indenones

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