Development of catalytic reactions triggered by addition of arylrhodium(I) species across alkynes

Tomoya Miura, Masahiro Murakami

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)


There has been a considerable progress in the development of the rhodium (I)-catalyzed carbon-carbon bond forming reactions using organoboronic acids during the past decade. In most cases, the intermediate organorhodium(D complexes are hydrolyzed without being used for a further reaction despite their potential usefulness for carbon-carbon bond formation. We then envisaged that the intramolecular trapping of the intermediate species might be feasible if an accepting functional group was placed at an appropriate position in the molecule. In this article, we describe various types of cascade reactions triggered by addition of arylrhodium(D species across alkynes. The resulting alkenylrhodium(I) intermediate subsequently undergoes either (type-i) intramolecular addition across a carbon-heteroatom multiple bond, (type-ii) intramolecular addition across a carbon-carbon multiple bond, or (type-iii) β-oxygen elimination. It is also illustrated that the reactivity order of organorhodium(I) intermediates toward nitriles and esters is opposite to that of organolithium and organomagnesium reagents. The synthetic potential of the rhodium-catalyzed reaction of alkynyl oxiranes with arylboronic acids was demonstrated by applying to the total synthesis of (±)-Boivinianin B.

Original languageEnglish
Pages (from-to)745-754
Number of pages10
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Issue number7
Publication statusPublished - Jul 2010
Externally publishedYes


  • Addition reaction
  • Alkenylrhodium (I) intermediate
  • Alkyne
  • Arylrhodium(I) species
  • Cascade reaction
  • Organoboronic acid
  • Rhodium

ASJC Scopus subject areas

  • Organic Chemistry


Dive into the research topics of 'Development of catalytic reactions triggered by addition of arylrhodium(I) species across alkynes'. Together they form a unique fingerprint.

Cite this