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

doi:10.1142/S108842460400057X

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 journal › Article › peer-review

26 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 language	English
Pages (from-to)	1222-1227
Number of pages	6
Journal	Journal of Porphyrins and Phthalocyanines
Volume	8
Issue number	10
DOIs	https://doi.org/10.1142/S108842460400057X
Publication status	Published - 2004
Externally published	Yes

Keywords

Bromination
Organometallic
Palladium
Porphyrins

ASJC Scopus subject areas

Chemistry(all)

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10.1142/S108842460400057X

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@article{26512391ebef499c88e292274534724b,

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

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.",

keywords = "Bromination, Organometallic, Palladium, Porphyrins",

author = "Aiko Kato and Hartnell, {Regan D.} and Masahiro Yamashita and Hiroshi Miyasaka and Sugiura, {Ken Ichi} and Arnold, {Dennis P.}",

note = "Funding Information: R.D.H. thanks the Faculty of Science, Queensland University of Technology, for a Post-Graduate Scholarship. This work was supported in part by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan and Japan Science and Technology Corporation (to K.-i.S., M.Y. and H.M.). The authors thank Mr. Hitoshi Yamada, The Institute of Scientific and Industrial Research, Osaka University, for the FAB-MASS spectra measurement.",

year = "2004",

doi = "10.1142/S108842460400057X",

language = "English",

volume = "8",

pages = "1222--1227",

journal = "Journal of Porphyrins and Phthalocyanines",

issn = "1088-4246",

publisher = "Society of Porphyrins and Phthalocyanines (SPP)",

number = "10",

}

TY - JOUR

T1 - Selective meso-monobromination of 5,15-diarylporphyrins via organopalladium porphyrins

AU - Kato, Aiko

AU - Hartnell, Regan D.

AU - Yamashita, Masahiro

AU - Miyasaka, Hiroshi

AU - Sugiura, Ken Ichi

AU - Arnold, Dennis P.

N1 - Funding Information: R.D.H. thanks the Faculty of Science, Queensland University of Technology, for a Post-Graduate Scholarship. This work was supported in part by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan and Japan Science and Technology Corporation (to K.-i.S., M.Y. and H.M.). The authors thank Mr. Hitoshi Yamada, The Institute of Scientific and Industrial Research, Osaka University, for the FAB-MASS spectra measurement.

PY - 2004

Y1 - 2004

N2 - 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.

AB - 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.

KW - Bromination

KW - Organometallic

KW - Palladium

KW - Porphyrins

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EP - 1227

JO - Journal of Porphyrins and Phthalocyanines

JF - Journal of Porphyrins and Phthalocyanines

SN - 1088-4246

IS - 10

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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