Cathodic reductive couplings and hydrogenations of alkenes and alkynes catalyzed by the B12 model complex

Hisashi Shimakoshi, Zhongli Luo, Kazuya Tomita, Yoshio Hisaeda

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The reductive coupling and hydrogenation of alkenes were catalyzed by the B12 model complex, heptamethyl cobyrinate perchlorate (1), in the presence of acid during electrolysis at −0.7 V vs. Ag/AgCl in acetonitrile. Conjugated alkenes showed a good reactivity during electrolysis to form reduced products. The product distributions were dependent on the substituents at the C[dbnd]C bond of the alkenes. ESR spin-trapping experiments using 5,5-dimethylpyrroline N-oxide (DMPO) revealed that the cobalt-hydrogen complex (Co–H complex) should be formed during the electrolysis and it functioned as an intermediate for the alkene reduction. The electrolysis was also applied to an alkyne, such as phenylacetylene, to form 2,3-diphenylbutane (racemic and meso) and ethylbenzene via styrene as reductive coupling and hydrogenated products, respectively.

Original languageEnglish
Pages (from-to)71-77
Number of pages7
JournalJournal of Organometallic Chemistry
Volume839
DOIs
Publication statusPublished - Jan 1 2017

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Electrolysis
Hydrogenation
Alkynes
Alkenes
alkynes
electrolysis
alkenes
Olefins
hydrogenation
products
Spin Trapping
Styrene
Ethylbenzene
perchlorates
Cobalt
Acetonitrile
styrenes
Oxides
acetonitrile
Paramagnetic resonance

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

Cathodic reductive couplings and hydrogenations of alkenes and alkynes catalyzed by the B12 model complex. / Shimakoshi, Hisashi; Luo, Zhongli; Tomita, Kazuya; Hisaeda, Yoshio.

In: Journal of Organometallic Chemistry, Vol. 839, 01.01.2017, p. 71-77.

Research output: Contribution to journalArticle

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