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A trinuclear chromium(iii) chlorocarbyne.

Takashi Kurogi1, Keiichi Irifune1, Takahiro Enoki1

  • 1Division of Applied Chemistry, Graduate School of National Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan. tkurogi@okayama-u.ac.jp ktakai@cc.okayama-u.ac.jp.

Chemical Communications (Cambridge, England)
|April 28, 2021
PubMed
Summary

A novel trinuclear chromium carbyne complex was synthesized from carbon tetrachloride. This complex reacts with aldehydes to produce chloroallylic alcohols and terminal alkynes through a proposed mechanism involving an alpha-chlorovinyl intermediate.

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Area of Science:

  • Organometallic Chemistry
  • Inorganic Chemistry
  • Organic Synthesis

Background:

  • Chromium complexes are versatile reagents in organic synthesis.
  • Carbyne complexes offer unique reactivity for C-C bond formation.
  • Carbon tetrachloride is a common precursor in chemical reactions.

Purpose of the Study:

  • To synthesize and characterize a novel trinuclear chromium carbyne complex.
  • To investigate the reactivity of the chromium carbyne complex with aldehydes.
  • To elucidate the reaction mechanism for the formation of chloroallylic alcohols and terminal alkynes.

Main Methods:

  • Reduction of carbon tetrachloride using chromium(II) chloride in tetrahydrofuran (THF).
  • Reaction of the synthesized trinuclear chromium carbyne complex with various aldehydes.
  • Mechanistic studies involving isotopic labeling and intermediate trapping (implied).

Main Results:

  • Successful synthesis of a trinuclear chromium(III) carbyne complex, [CrCl(thf)2]3(μ3-CCl)(μ-Cl)3.
  • The complex reacts with aldehydes to yield chloroallylic alcohols and terminal alkynes.
  • A mechanistic study suggests two competing pathways involving an α-chlorovinyl intermediate.

Conclusions:

  • The trinuclear chromium carbyne complex is a viable precursor for synthesizing chloroallylic alcohols and terminal alkynes.
  • The reaction proceeds via a mechanism involving an α-chlorovinyl intermediate, with evidence for two competitive pathways.
  • This study expands the synthetic utility of chromium carbyne complexes in organic chemistry.