Abstract
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.
| Language | English |
|---|---|
| Pages | 4492-4496 |
| Number of pages | 5 |
| Journal | Agewandte Chemie-International Edition |
| Volume | 55 |
| Early online date | 3 Mar 2016 |
| Publication status | Published - 2016 |
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Keywords
- pyridinecarbinol
- reduction
- electron transfer
- radical chain
- electron donor
- coupling
Cite this
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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 journal › Article
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
T2 - Angewandte Chemie International Edition
JF - Angewandte Chemie International Edition
SN - 1433-7851
ER -