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

Literature Information

Publication Date 2021-10-05
DOI 10.1039/D1QO01280K
Impact Factor 5.281
Authors

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


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Abstract

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.

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