Cationic Rhodium(I)-Catalyzed Carbonylative [2+2+1] Cycloaddition of Diynes

Tsumoru Morimoto*, Jing Wen Jia, Yoshiko Yamaguchi, Hiroki Tanimoto, Kiyomi Kakiuchi

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

We describe Rh(I)-catalyzed carbonylative [2+2+1] cycloaddition reactions of diynes with CO to give cyclopentadienone derivatives (CPDs). Previous reports on the use of neutral rhodium(I) complexes, such as [RhCl(cod)]2 and RhCl(PPh3)3, indicate that no CPD products are formed or that they are produced in low yields, even at elevated temperatures. The reaction described herein, which uses a cationic rhodium(I) complex, [Rh(cod)2]BF4, as a catalyst, proceeds smoothly at room temperature to give cyclopentadienone derivatives. The key to this is the use the cationic rhodium(I) complex as a catalyst, which produces an additional coordination site on the rhodium for the substrate (a diyne) to approach, than neutral rhodium complexes.

Original languageEnglish
Pages (from-to)1778-1782
Number of pages5
JournalAsian Journal of Organic Chemistry
Volume9
Issue number11
DOIs
StatePublished - 2020/11

Keywords

  • [2+2+1] cycloaddition
  • carbon monoxide
  • cyclopentadienones
  • diynes
  • rhodium

ASJC Scopus subject areas

  • Organic Chemistry

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