Rhodium(I)-catalyzed reactions via carbon-hydrogen bond cleavage

Takanori Shibata*

*Corresponding author for this work

Research output: Chapter in Book/Report/Conference proceedingChapter


This chapter focuses on Rh(I)-catalyzed synthetic transformations initiated by carbon-hydrogen (C-H) bond cleavage. The Ru-catalyzed carbonyl-directed C-H alkylation by alkenes is a monumental achievement in organic chemistry. In this reaction, a nitrogen-containing moiety was commonly used as an efficient directing group. Alkynes are conventional coupling partners in C-H activation and alkenylated products are obtained with perfect atom economy. C-H bond cleavage along with carbon-carbon bond-forming reactions provides synthetically useful compounds in one pot. While the metalation of organohalides and subsequent reaction with trialkyl borate is a conventional protocol for the preparation of organoboron compounds, C-H borylation is a more direct and atom-economical approach. Aryl and alkyl silanes are synthetically important because they are functional molecules in themselves and are useful intermediates for further transformations. Among the various approaches to the synthesis of silane-containing compounds, dehydrogenative C-H/Si-H coupling is an atom-economical protocol.

Original languageEnglish
Title of host publicationRhodium Catalysis in Organic Synthesis
Subtitle of host publicationMethods and Reactions
Number of pages21
ISBN (Electronic)9783527811878
ISBN (Print)9783527343645
Publication statusPublished - 2018 Dec 28


  • Alkyl silanes
  • C-H bond cleavage
  • C-H borylation
  • Carbon-carbon bond-forming reactions
  • Rh(I)-catalyzed synthetic transformations
  • Ru-catalyzed carbonyl-directed C-H alkylation

ASJC Scopus subject areas

  • Chemistry(all)


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