Bifunctional catalysts based on m-phenylene-bridged porphyrin dimer and trimer platforms: Synthesis of cyclic carbonates from carbon dioxide and epoxides

Chihiro Maeda, Tomoya Taniguchi, Kanae Ogawa, Tadashi Ema

Research output: Contribution to journalArticle

166 Citations (Scopus)

Abstract

Highly active bifunctional diporphyrin and triporphyrin catalysts were synthesized through Stille coupling reactions. As compared with a porphyrin monomer, both exhibited improved catalytic activities for the reaction of CO2 with epoxides to form cyclic carbonates, because of the multiple catalytic sites which cooperatively activate the epoxide. Catalytic activities were carefully investigated by controlling temperature, reaction time, and catalyst loading, and very high turnover number and turnover frequency were obtained: 220000 and 46000 h-1, respectively, for the magnesium catalyst, and 310000 and 40000 h-1, respectively, for the zinc catalyst. Results obtained with a zinc/free-base hybrid diporphyrin catalyst demonstrated that the Br- ions on the adjacent porphyrin moiety also function as nucleophiles.

Original languageEnglish
Pages (from-to)134-138
Number of pages5
JournalAngewandte Chemie - International Edition
Volume54
Issue number1
DOIs
Publication statusPublished - Jan 2 2015

Keywords

  • Carbon dioxide fixation
  • Cyclic carbonates
  • Homogeneous catalysis
  • Porphyrinoids
  • Zinc

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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