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

Kato, Aiko, Hartnell, Regan D., Yamashita, Masahiro, Miyasaka, Hiroshi, Sugiura, Ken-ichi, & Arnold, Dennis P. (2004) Selective meso-monobromination of 5,15-diarylporphyrins via organopalladium porphyrins. Journal of Porphyrins and Phthalocyanines, 8(10), pp. 1222-1227.


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.

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20 citations in Scopus
19 citations in Web of Science®
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ID Code: 1013
Item Type: Journal Article
Refereed: Yes
Additional URLs:
Keywords: porphyrins, organometallic, palladium, bromination
ISSN: 1088-4246
Subjects: Australian and New Zealand Standard Research Classification > CHEMICAL SCIENCE (030000) > OTHER CHEMICAL SCIENCES (039900) > Organometallic Chemistry (039904)
Divisions: Past > QUT Faculties & Divisions > Faculty of Science and Technology
Copyright Owner: Copyright 2004 Society of Porphyrins and Phthalocyanines
Copyright Statement: Reproduced in accordance with the copyright policy of the publisher.
Deposited On: 12 Apr 2005 00:00
Last Modified: 29 Feb 2012 13:30

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