Double deprotonation of pyridinols generates potent organic electron donor initiators for haloarene-arene coupling

Joshua P Barham, Graeme Coulthard, Ryan G Kane, Nathan Delgado, Matthew P John, John A Murphy

Research output: Contribution to journalArticle

46 Citations (Scopus)

Abstract

Transition metal-free couplings of haloarenes with arenes, triggered by the use of alkali metal alkoxides in the presence of an organic additive, are receiving significant attention in the literature. Most of the known organic additives effect coupling of iodoarenes, but not bromoarenes, to arenes. Recently Kwong showed that 2-pyridinecarbinol 11 extends the reaction to aryl bromides. This paper
investigates the mechanism, and reports evidence for dianions derived from 11 as electron donors to initiate the reaction. It also proposes routes by which electron-poor benzoyl derivatives can be transformed into electron donors to initiate these reactions.
LanguageEnglish
Pages4492-4496
Number of pages5
JournalAgewandte Chemie-International Edition
Volume55
Early online date3 Mar 2016
Publication statusPublished - 2016

Fingerprint

Deprotonation
Electrons
Alkali Metals
Alkali metals
Bromides
Transition metals
Derivatives

Keywords

  • pyridinecarbinol
  • reduction
  • electron transfer
  • radical chain
  • electron donor
  • coupling

Cite this

Barham, Joshua P ; Coulthard, Graeme ; Kane, Ryan G ; Delgado, Nathan ; John, Matthew P ; Murphy, John A. / Double deprotonation of pyridinols generates potent organic electron donor initiators for haloarene-arene coupling. In: Agewandte Chemie-International Edition. 2016 ; Vol. 55. pp. 4492-4496.
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abstract = "Transition metal-free couplings of haloarenes with arenes, triggered by the use of alkali metal alkoxides in the presence of an organic additive, are receiving significant attention in the literature. Most of the known organic additives effect coupling of iodoarenes, but not bromoarenes, to arenes. Recently Kwong showed that 2-pyridinecarbinol 11 extends the reaction to aryl bromides. This paperinvestigates the mechanism, and reports evidence for dianions derived from 11 as electron donors to initiate the reaction. It also proposes routes by which electron-poor benzoyl derivatives can be transformed into electron donors to initiate these reactions.",
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Double deprotonation of pyridinols generates potent organic electron donor initiators for haloarene-arene coupling. / Barham, Joshua P; Coulthard, Graeme; Kane, Ryan G; Delgado, Nathan; John, Matthew P; Murphy, John A.

In: Agewandte Chemie-International Edition, Vol. 55, 2016, p. 4492-4496.

Research output: Contribution to journalArticle

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AB - Transition metal-free couplings of haloarenes with arenes, triggered by the use of alkali metal alkoxides in the presence of an organic additive, are receiving significant attention in the literature. Most of the known organic additives effect coupling of iodoarenes, but not bromoarenes, to arenes. Recently Kwong showed that 2-pyridinecarbinol 11 extends the reaction to aryl bromides. This paperinvestigates the mechanism, and reports evidence for dianions derived from 11 as electron donors to initiate the reaction. It also proposes routes by which electron-poor benzoyl derivatives can be transformed into electron donors to initiate these reactions.

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KW - electron transfer

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