Selective meso-monobromination of 5,15-diarylporphyrins via organopalladium porphyrins

Aiko Kato, Regan D. Hartnell, Masahiro Yamashita, Hiroshi Miyasaka, Ken Ichi Sugiura, Dennis P. Arnold

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)


The selective meso-monobromination of 5,15-diarylporphyrins is difficult to achieve and extensive chromatography is required to obtain pure products. A sequence of (i) dibromination, (ii) selective monoinsertion of Pd(dppe) (dppe = 1,2-bis(diphenylphosphino)ethane) and (iii) hydrodepalladation using methanolic base affords pure monobromoporphyrins in typically ≥ 60% overall yield without isolation of the organopalladium porphyrin. Monobromo derivatives of even highly lipophilic 5,15-diarylporphyrins are thus readily available without tedious, expensive and environmentally undesirable chromatography.

Original languageEnglish
Pages (from-to)1222-1227
Number of pages6
JournalJournal of Porphyrins and Phthalocyanines
Issue number10
Publication statusPublished - 2004
Externally publishedYes


  • Bromination
  • Organometallic
  • Palladium
  • Porphyrins

ASJC Scopus subject areas

  • Chemistry(all)


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