Substituent effects on stoichiometric and catalytic cleavage of carbon-nitrogen bonds in aniline derivatives by ruthenium-phosphine complexes

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Abstract

The reactivity of various o-acylaniline derivatives with ruthenium complexes was examined. The reaction of o-acylanilines with RuH 2(CO)(PPh3)3 (1) or an activated ruthenium species formulated as "Ru(CO)(PPh3)3" (4) gave amido hydrido complexes 3 and aryl amido complexes 6 formed via N-H and C-N bond cleavage, respectively. Addition of olefins, such as vinylsilanes, accelerates the C-N bond cleavage. The aryl amido complexes 6 can provide the C-N arylation product upon treatment with arylboronates. The relative reactivity of o-acylanilines bearing various substituents was investigated by competition experiments, and it was found that electron-donating substituents increase the relative facileness of the C-N bond cleavage in both stoichiometric and catalytic reactions. The trend observed here is different from the one observed for the previously reported tantalum-mediated C-N bond cleavage.

Original languageEnglish
Pages (from-to)682-690
Number of pages9
JournalOrganometallics
Volume32
Issue number2
DOIs
Publication statusPublished - 2013 Jan 28

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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