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

Giuseppe Nocera; John A. Murphy

doi:10.1055/s-0039-1690614

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

Giuseppe Nocera, John A. Murphy

Pure And Applied Chemistry

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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.

Original language	English
Number of pages	10
Journal	Synthesis
Volume	51
Early online date	13 Sept 2019
DOIs	https://doi.org/10.1055/s-0039-1690614
Publication status	E-pub ahead of print - 13 Sept 2019

Keywords

electron transfer
initiation
BHAS coupling
organic electron donor
radical reaction

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Nocera-Murphy-Synthesis-2019-Ground-state-cross-coupling-of-haloarenes-with-arenesAccepted author manuscript, 854 KB

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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.",

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AU - Murphy, John A.

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Y1 - 2019/9/13

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

M3 - Article

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JO - Synthesis

JF - Synthesis

ER -

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

Abstract

Keywords

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