Issue 20, 2007
From the journal:

Chemical Communications

Unusual regioselective mercuration of metalloporphyrins and its potential applications†

Ken-ichi Sugiura,*ab   Aiko Kato,ac   Kentaro Iwasaki,d   Hitoshi Miyasaka,ae   Masahiro Yamashita,abe   Shojun Hinodf  and  Dennis P. Arnold*c  

* Corresponding authors

a Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, 1-1 Minami-Ohsawa, Hachi-Oji, Japan
E-mail: sugiura@porphyrin.jp
Fax: +81 42-677-2525
Tel: +81 42-677-2550

b CREST, Japan Science and Technology Corporation, Kawaguchi Center Building, 4-1-8 Honcho, Kawaguchi, Japan

c School of Physical and Chemical Sciences, Queensland University of Technology, GPO Box 2434, Australia
E-mail: d.arnold@qut.edu.au
Fax: +61 7-3864-1804
Tel: +61 7-3864-2482

d Department of Information and Image Science, Faculty of Engineering, Chiba University, Inageku, Japan

e Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki-Aza-Aoba, Aoba-ku, Japan

f Department of Material Science and Biotechnology, Graduate School of Engineering, Ehime University, Bunkyo-Cho 3, Matsuyama, Japan

Abstract

The reaction of Hg(CF3CO2)2 with metalloporphyrins produces mercurated porphyrins regioselectively, the reaction, surprisingly occurring at the most hindered βB-position; this behavior is in marked contrast to the usual electrophilic substitution reactions of porphyrins, whose reactions produce meso-substituted porphyrins; the obtained mercurated porphyrins are active to transition metal-catalyzed coupling reactions, such as the Mizoroki–Heck reaction.

Graphical abstract: Unusual regioselective mercuration of metalloporphyrins and its potential applications

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Article information

DOI
https://doi.org/10.1039/B618464B
Article type
Communication
Submitted
19 Dec 2006
Accepted
09 Mar 2007
First published
27 Mar 2007

Chem. Commun., 2007, 2046-2047

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Unusual regioselective mercuration of metalloporphyrins and its potential applications

K. Sugiura, A. Kato, K. Iwasaki, H. Miyasaka, M. Yamashita, S. Hino and D. P. Arnold, Chem. Commun., 2007, 2046 DOI: 10.1039/B618464B

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