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December 10, 2025The Journal of Organic Chemistry2 citations

TMSCl-Promoted Cascade Sulfonylation/Cyclization of Indole-Linked Propargylic Alcohols with Sodium Sulfinates for the Construction of Sulfonylated Indeno1,2- b indoles

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MLMeng LiangMDMei DongRYRuchun Yang

Key Points

  • The study aims to develop a metal-free method for constructing sulfonylated indeno[1,2-b]indoles.
  • Utilized TMSCl to promote cascade sulfonylation and cyclization
  • Employed indole-linked propargylic alcohols and sodium sulfinates
  • Used allenyl sulfones as key intermediates during the transformation
  • Successfully generated sulfonylated indeno[1,2-b]indoles with a quaternary carbon stereocenter
  • Achieved high regioselectivity in the cascade reaction
  • Demonstrated a new pathway compared to conventional cyclization methods

Abstract

A novel metal-free protocol for the construction of sulfonylated indeno1,2-bindoles with a highly decorated quaternary carbon stereocenter was developed through the TMSCl-promoted cascade sulfonylation/cyclization of indole-linked propargylic alcohols and sodium sulfinates. The novel transformation involved allenyl sulfones as the key intermediates, followed by 5-exo-trig cyclization to achieve the desired products. Notably, this cascade reaction proceeded via a new pathway with high regioselectivity of the allenyl sulfone intermediate compared with the conventional cyclization pathway.

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Cite This Study

Liang et al. (2025) studied this question.

synapsesocial.com/papers/69401d472d562116f28f8550https://doi.org/10.1021/acs.joc.5c02183
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