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

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

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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
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 28.12.2020
Royal Society of Chemistry
Subjects
Bromination
Chemistry
Chemistry, Organic
Crystallography
Physical Sciences
Porphyrins
Science & Technology
Zinc
H BOND ACTIVATION
FUNCTIONALIZATION
REARRANGEMENT
HIGH-VALENT METALLOPORPHYRIN
MANGANESE
PHOTOSENSITIZERS
MESOSUBSTITUTED PORPHYRINS
FACILE
SILYLATION
BORYLATION
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Summary:A convenient method for the preparation of meso,beta-dual-functionalized porphyrin was developed. The bromination of zincated beta-silylporphyrin with NBS selectively yielded meso-bromo-beta-silylporphyrin, whereas, the bromination of free-base beta-silylporphyrin selectively yielded beta-bromoporphyrin via an ipso-substitution of the silyl group. These meso,beta-dual-functionalized porphyrins could be used as multipurpose synthons for fabricating various porphyrin derivatives.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob02262d