Ground state cross-coupling of haloarenes with arenes initiated by organic electron donors, formed in situ: an overview

Research output: Contribution to journalArticle

Abstract

Many reactions have been discovered that lead to coupling of haloarenes to arenes using potassium tert-butoxide as the base, and one of a variety of organic compounds as an additive. The organic additive reacts with the base to form a strong organic electron donor in situ that initiates a base-induced homolytic aromatic substitution (BHAS) coupling reaction, by converting the haloarene into an aryl radical. This brief report presents an overview of the wide range of organic additives that can be used, and the organic electron donors that they form.
LanguageEnglish
Number of pages10
JournalSynthesis
Volume51
Early online date13 Sep 2019
DOIs
Publication statusE-pub ahead of print - 13 Sep 2019

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Ground state
Electrons
Organic compounds
Potassium
Substitution reactions
potassium tert-butoxide

Keywords

  • electron transfer
  • initiation
  • BHAS coupling
  • organic electron donor
  • radical reaction

Cite this

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title = "Ground state cross-coupling of haloarenes with arenes initiated by organic electron donors, formed in situ: an overview",
abstract = "Many reactions have been discovered that lead to coupling of haloarenes to arenes using potassium tert-butoxide as the base, and one of a variety of organic compounds as an additive. The organic additive reacts with the base to form a strong organic electron donor in situ that initiates a base-induced homolytic aromatic substitution (BHAS) coupling reaction, by converting the haloarene into an aryl radical. This brief report presents an overview of the wide range of organic additives that can be used, and the organic electron donors that they form.",
keywords = "electron transfer, initiation, BHAS coupling, organic electron donor, radical reaction",
author = "Giuseppe Nocera and Murphy, {John A.}",
year = "2019",
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doi = "10.1055/s-0039-1690614",
language = "English",
volume = "51",
journal = "Synthesis",
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publisher = "Georg Thieme Verlag",

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N2 - Many reactions have been discovered that lead to coupling of haloarenes to arenes using potassium tert-butoxide as the base, and one of a variety of organic compounds as an additive. The organic additive reacts with the base to form a strong organic electron donor in situ that initiates a base-induced homolytic aromatic substitution (BHAS) coupling reaction, by converting the haloarene into an aryl radical. This brief report presents an overview of the wide range of organic additives that can be used, and the organic electron donors that they form.

AB - Many reactions have been discovered that lead to coupling of haloarenes to arenes using potassium tert-butoxide as the base, and one of a variety of organic compounds as an additive. The organic additive reacts with the base to form a strong organic electron donor in situ that initiates a base-induced homolytic aromatic substitution (BHAS) coupling reaction, by converting the haloarene into an aryl radical. This brief report presents an overview of the wide range of organic additives that can be used, and the organic electron donors that they form.

KW - electron transfer

KW - initiation

KW - BHAS coupling

KW - organic electron donor

KW - radical reaction

U2 - 10.1055/s-0039-1690614

DO - 10.1055/s-0039-1690614

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