Development of a catalytic electron transfer system mediated by transition metal ate complexes: Applicability and tunability of electron-releasing potential for organic transformations

Masanobu Uchiyama, Yotaro Matsumoto, Shinji Nakamura, Tomohiko Ohwada, Nagao Kobayashi, Natsuno Yamashita, Atsushi Matsumiya, Takao Sakamoto

Research output: Contribution to journalArticle

52 Citations (Scopus)

Abstract

We have developed a catalytic electron transfer (ET) system composed of a transition metal ate complex (Me 3M(II)Li; M = Co(II), Mn(II), Fe(II)) and magnesium. This system (catalytic Me 3M(II)Li/Mg) turned out to be effective for various ET reactions, such as the desulfonylation of N-phenylsulfonyl amides, and others (the chemoselective cleavage of O-allyl groups, the reduction of nitro groups, the partial reduction of diketones, and the reductive coupling of diphenyliodonium salt). The ET ability of this system can be tuned by changing the ligands of the ate complexes. This tunability was experimentally and electrochemically demonstrated: alkoxy-ligated and dianion-type ET ate complexes showed attenuated and enhanced reducing abilities, respectively. The modification of the ET abilities was evaluated by means of electrochemical measurements and chemical reactions. These results provide a basis for the design of various tailor-made ET ate complexes.

Original languageEnglish
Pages (from-to)8755-8759
Number of pages5
JournalJournal of the American Chemical Society
Volume126
Issue number28
DOIs
Publication statusPublished - 2004 Jul 21
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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