Nanoporous Gold-Catalyzed Diboration of Methylenecyclopropanes via a Distal Bond Cleavage

Qiang Chen, Xuan Zhang, Shuo Su, Zhanqiang Xu, Na Li, Yiya Li, Han Zhou, Ming Bao, Yoshinori Yamamoto, Tienan Jin

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

We have demonstrated that nanoporous gold (AuNPore) is an efficient catalyst to promote the selective diboration of methylenecyclopropanes (MCPs) in a heterogeneous manner. Notably, the diboration takes place via a regioselective cleavage of the distal bond of the cyclopropane ring exclusively by AuNPore without using any additives. The experimental results and computational studies of the mechanism indicate that the present diboration proceeds through the formation of a relatively stable trimethylenemethane intermediate on the AuNPore surface with increased negative charges on trimethylene carbons, giving rise to the subsequent diboration selectively.

Original languageEnglish
Pages (from-to)5901-5906
Number of pages6
JournalACS Catalysis
Volume8
Issue number7
DOIs
Publication statusPublished - 2018 Jul 6

Keywords

  • diboration
  • distal bond cleavage
  • methylenecyclopropanes
  • nanoporous gold catalysis
  • trimethylenemethane

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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  • Cite this

    Chen, Q., Zhang, X., Su, S., Xu, Z., Li, N., Li, Y., Zhou, H., Bao, M., Yamamoto, Y., & Jin, T. (2018). Nanoporous Gold-Catalyzed Diboration of Methylenecyclopropanes via a Distal Bond Cleavage. ACS Catalysis, 8(7), 5901-5906. https://doi.org/10.1021/acscatal.8b01193