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February 2, 2026Organic Letters0 citations

Palladium-Catalyzed Regiodivergent 4 + 2 Cycloaddition of Benzosilacyclobutenes with Phenylpropiolonitriles

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XWXing-Ben WangJGJun-Jie GuoMSMing-Hao SHEN

Key Points

  • To develop a ligand-controlled palladium-catalyzed reaction that produces distinct classes of dihydrobenzo[c]silane derivatives from a common substrate.
  • Implemented a palladium-catalyzed regiodivergent (4 + 2) cycloaddition reaction.
  • Used benzosilacyclobutenes and phenylpropiolonitriles as substrates.
  • Modulated catalyst systems with different phosphine ligands to steer selectivity.
  • Achieved two distinct classes of dihydrobenzo[c]silane derivatives through ligand modification.
  • Obtained high efficiency and excellent selectivity during the reactions.
  • Provided a versatile platform for synthesizing structurally diverse silaheterocycles.

Abstract

The controlled diversification of reaction pathways from a common substrate through precise modulation of catalyst systems represents a persistent challenge in catalysis and synthetic chemistry. Herein, we report a ligand-controlled Pd-catalyzed regiodivergent (4 + 2) silacyclization between benzosilacyclobutenes and unsymmetrical phenylpropiolonitriles, which selectively affords two distinct classes of dihydrobenzocsilane derivatives. Each phosphine ligand steers the reaction along a unique pathway, enabling exceptional control over chemoselectivity. Through steric and electronic modulation of the ligands, both high efficiency and excellent selectivity are achieved. This strategy with divergent catalysis provides a versatile platform for the structurally diverse synthesis of silaheterocycles, with promising implications for atom-economical synthesis and functional materials.

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Cite This Study

Wang et al. (2026) studied this question.

synapsesocial.com/papers/6980fe68c1c9540dea810696https://doi.org/10.1021/acs.orglett.5c05319
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