HIGHLY VERSATILE METHODS FOR THE SYNTHESIS OF QUINONYLPORPHYRINS VIA BENZANNULATION OF FISCHER CARBENE COMPLEXES AND PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS
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AbstractCovalently-Linked porphyrin mono- and tetraquinones with well-defined distances and orientations were synthesized on the basis of two synthetic approaches. (1) The benzannulation of Fischer carbene complexes with meso-(alkynylphenyl)-substituted porphyrins, followed by oxidation, produced quinone-linked porphyrins, with both electron-donating and -withdrawing substituents on the quinone moieties. (2) The palladium-catalyzed Suzuki cross-coupling reactions of (2,5-dimethoxyphenyl)boronic acid with porphyrin meso-aryl triflates and aryl bromides, followed by subsequent demethylation and oxidation, gave meso-(benzoquinonylphenyl)-substituted porphyrins.
All Author(s) ListCHAN CS, TSE AKS, CHAN KS
Journal nameJournal of Organic Chemistry
Year1994
Month10
Day7
Volume Number59
Issue Number20
PublisherAMER CHEMICAL SOC
Pages6084 - 6089
ISSN0022-3263
LanguagesEnglish-United Kingdom
Web of Science Subject CategoriesChemistry; Chemistry, Organic; CHEMISTRY, ORGANIC

Last updated on 2020-29-05 at 01:14