Central zinc metal-controlled regioselective -bromination of β-silylporphyrins-rapid access to ,β-dual-functionalized porphyrins

A convenient method for the preparation of meso ,β-dual-functionalized porphyrin was developed. The bromination of zincated β-silylporphyrin with NBS selectively yielded meso -bromo-β-silylporphyrin, whereas, the bromination of free-base β-silylporphyrin selectively yielded β-bromoporphyrin via an i...

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Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 18; no. 48; pp. 9791 - 9795
Main Authors Hayashi, Satoshi, Takamatsu, Rina, Takeda, Shiori, Noji, Masahiro, Takanami, Toshikatsu
Format Journal Article
Published 23.12.2020
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Summary:A convenient method for the preparation of meso ,β-dual-functionalized porphyrin was developed. The bromination of zincated β-silylporphyrin with NBS selectively yielded meso -bromo-β-silylporphyrin, whereas, the bromination of free-base β-silylporphyrin selectively yielded β-bromoporphyrin via an ipso -substitution of the silyl group. These meso ,β-dual-functionalized porphyrins could be used as multipurpose synthons for fabricating various porphyrin derivatives. A convenient method for preparing meso ,β-dual-functionalized porphyrin through a central zinc metal-controlled regioselective bromination of zincated β-silylporphyrin was developed.
Bibliography:CCDC
For ESI and crystallographic data in CIF or other electronic format see DOI
10.1039/d0ob02262d
Electronic supplementary information (ESI) available: Synthesis and characterization data of new compounds, and X-ray crystallographic data for
Zn-3c
2035888
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob02262d