ARTICLE

Pd-catalyzed [3+2] Cycloaddition/Dearomatization of Indole-3-carboxylates with Trimethylenemethane

  • Qing-Xia Zhang ,
  • Jia-Hao Xie ,
  • Qing Gu ,
  • Shu-Li You
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  • New Cornerstone Science Laboratory, State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Received date: 2026-02-27

  Revised date: 2026-03-21

  Online published: 2026-04-17

Supported by

NSFC (22393890), Science and Technology Commission of Shanghai Municipality (23JC1404500) and Shanghai Pilot Program for Basic Research. S.-L.Y. acknowledges the support from New Cornerstone Science Foundation.

Abstract

A formal [3+2] cycloaddition between indole-3-carboxylate derivatives and trimethylenemethane (TMM) donor is disclosed. The reaction proceeds smoothly in toluene at ambient conditions via a Pd-catalyzed dearomatization process, delivering a series of substituted 2,3-fused cyclopentannulated indolines (up to 99% yield). The reaction exhibits high functional group tolerance for indole derivatives under the standard conditions. Remarkably, the synthetic utility of this method was demonstrated by transformation of the products such as hydrolysis of ester, removal of Ts group, Sonogashira coupling reaction and reduction of ester and halogen.

Cite this article

Qing-Xia Zhang , Jia-Hao Xie , Qing Gu , Shu-Li You . Pd-catalyzed [3+2] Cycloaddition/Dearomatization of Indole-3-carboxylates with Trimethylenemethane[J]. Chinese Journal of Organic Chemistry, 0 : 202602022 -202602022 . DOI: 10.6023/cjoc202602022

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