Aryl carbon-chlorine (Ar-Cl) and aryl carbon-fluorine (Ar-F) bond cleavages by rhodium porphyrins
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AbstractAryl carbon-chlorine (Ar-Cl) bond cleavage has been achieved with rhodium(III) tetrakis-4-tolylporphyrin chloride (Rh(ttp)Cl) to give Rh(ttp)Ar. For 4-chlorofluorobenzene, the aryl carbon-fluorine (Ar-F) bond cleavage competes with the Ar-Cl bond cleavage. Mechanistic investigations show that the Ar-Cl bond cleavage goes through metalloradical ipso-substitution mechanism, while the Ar-F bond cleavage goes through nucleophilic aromatic substitution. The selectivity of the Ar-F or Ar-Cl bond cleavage can be controlled by tuning the temperature and substrate concentration.
All Author(s) ListQian Y.Y., Lee M.H., Yang W., Chan K.S.
Journal nameJournal of Organometallic Chemistry
Year2015
Month6
Day3
Volume Number791
PublisherElsevier BV
Place of PublicationNetherlands
Pages82 - 89
ISSN0022-328X
eISSN1872-8561
LanguagesEnglish-United Kingdom
KeywordsCarbon-chlorine bond activation, Carbon-fluorine bond activation, Rhodium porphyrin

Last updated on 2020-27-10 at 02:59