C-C bond-forming reactions of ground-state aryl halides under reductive activation

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Abstract

Under basic conditions aryl halides can undergo SRN1 reactions, BHAS reactions and benzyne formations. Appropriate complex substrates afford an opportunity to study inherent selectivities. SRN1 reactions are usually favoured under photoactivated conditions, but this paper reports their success using ground-state and transition metal-free conditions. In benzene, the enolate salt 12, derived by deprotonation of diketopiperazine 11, behaves as an electron donor, and assists the initiation of the reactions, but in DMSO, it is not required. The outcomes are compared and contrasted with a recent photochemical study on similar substrates. A particular difference is the prevalence of hydride shuttle reactions under relatively mild thermal conditions.
Original languageEnglish
Pages (from-to)7875-7887
Number of pages13
JournalTetrahedron
Volume72
Issue number48
Early online date2 Jun 2016
DOIs
Publication statusPublished - 1 Dec 2016

Keywords

  • radical
  • coupling
  • electron transfer
  • BHAS
  • SRN1
  • hydride shuttle reactions
  • benzyne formations

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