Synthesis of ene-yne-enes by nickel-catalyzed double S(N)2' substitution of 1,6-dichlorohexa-2,4-diyne

  • Gongbao Wang
  • , Erik-Jan Lindeboom
  • , Chris van Heerewaarden
  • , Adriaan J. Minnaard*
  • *Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

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Abstract

1,6-Dichlorohexa-2,4-diyne undergoes nickel-catalyzed double substitution with aryl and alkenyl Grignard reagents to provide substituted ene-yne-enes. The reaction is formally an extension of the well-described S(N)2'-allylic and -propargylic substitution reactions but the mechanism is considerably more complex. The products might function as building blocks for conjugated polymers.

Original languageEnglish
Article numberC7CY00429J
Pages (from-to)2347-2355
Number of pages9
JournalCatalysis Science & Technology
Volume7
Issue number11
DOIs
Publication statusPublished - 7-Jun-2017

Keywords

  • ASYMMETRIC ALLYLIC ALKYLATION
  • ENANTIOSELECTIVE SYNTHESIS
  • GRIGNARD-REAGENTS
  • ALKYLZINC REAGENTS
  • ORGANIC HALIDES
  • COPPER
  • COMPLEXES
  • BOND
  • DESYMMETRIZATION
  • POLYDIACETYLENES

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