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Unusual regioselective mercuration of metalloporphyrins and its potential applications

Author:
Sugiura, Ken-ichi, Kato, Aiko, Iwasaki, Kentaro, Miyasaka, Hitoshi, Yamashita, Masahiro, Hino, Shojun, Arnold, Dennis P.
Source:
Chemical communications 2007 no.20 pp. 2046-2047
ISSN:
1364-548X
Subject:
Lewis acids, catalytic activity, chemical reactions, mercury, porphyrins, regioselectivity
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.
Agid:
6580822