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

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

Pure And Applied Chemistry

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52 Citations (Scopus)

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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 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.

Original language	English
Pages (from-to)	4492-4496
Number of pages	5
Journal	Agewandte Chemie-International Edition
Volume	55
Early online date	3 Mar 2016
Publication status	Published - 2016

Keywords

pyridinecarbinol
reduction
electron transfer
radical chain
electron donor
coupling

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@article{dbb2886edd65464780c9959b4cbe1ccd,

title = "Double deprotonation of pyridinols generates potent organic electron donor initiators for haloarene-arene coupling",

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.",

keywords = "pyridinecarbinol, reduction , electron transfer, radical chain , electron donor, coupling",

author = "Barham, {Joshua P} and Graeme Coulthard and Kane, {Ryan G} and Nathan Delgado and John, {Matthew P} and Murphy, {John A}",

note = "This is the peer reviewed version of the following article: Barham, J. P., Coulthard, G., Kane, R. G., Delgado, N., John, M. P., & Murphy, J. A. (2016). Double deprotonation of pyridinols generates potent organic electron donor initiators for haloarene-arene coupling. Angewandte Chemie., which has been published in final form at [Link to final article using the DOI]. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.",

year = "2016",

language = "English",

volume = "55",

pages = "4492--4496",

journal = "Angewandte Chemie International Edition",

issn = "1433-7851",

}

TY - JOUR

T1 - Double deprotonation of pyridinols generates potent organic electron donor initiators for haloarene-arene coupling

AU - Barham, Joshua P

AU - Coulthard, Graeme

AU - Kane, Ryan G

AU - Delgado, Nathan

AU - John, Matthew P

AU - Murphy, John A

N1 - This is the peer reviewed version of the following article: Barham, J. P., Coulthard, G., Kane, R. G., Delgado, N., John, M. P., & Murphy, J. A. (2016). Double deprotonation of pyridinols generates potent organic electron donor initiators for haloarene-arene coupling. Angewandte Chemie., which has been published in final form at [Link to final article using the DOI]. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.

PY - 2016

Y1 - 2016

N2 - 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.

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.

KW - pyridinecarbinol

KW - reduction

KW - electron transfer

KW - radical chain

KW - electron donor

KW - coupling

M3 - Article

VL - 55

SP - 4492

EP - 4496

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

SN - 1433-7851

ER -