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 journalArticle

27 Citations (Scopus)

Abstract

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
Volume8
Issue number10
DOIs
Publication statusPublished - 2004

Keywords

  • Bromination
  • Organometallic
  • Palladium
  • Porphyrins

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Dive into the research topics of 'Selective meso-monobromination of 5,15-diarylporphyrins via organopalladium porphyrins'. Together they form a unique fingerprint.

  • Cite this

    Kato, A., Hartnell, R. D., Yamashita, M., Miyasaka, H., Sugiura, K. I., & Arnold, D. P. (2004). Selective meso-monobromination of 5,15-diarylporphyrins via organopalladium porphyrins. Journal of Porphyrins and Phthalocyanines, 8(10), 1222-1227. https://doi.org/10.1142/S108842460400057X