Double deprotonation of pyridinols generates potent organic electron donor initiators for haloarene-arene coupling
Barham, Joshua P and Coulthard, Graeme and Kane, Ryan G and Delgado, Nathan and John, Matthew P and Murphy, John A (2016) Double deprotonation of pyridinols generates potent organic electron donor initiators for haloarene-arene coupling. Agewandte Chemie-International Edition, 55. pp. 4492-4496. ISSN 1521-3773
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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.
ORCID iDs
Barham, Joshua P ORCID: https://orcid.org/0000-0003-1675-9399, Coulthard, Graeme ORCID: https://orcid.org/0000-0002-4413-2828, Kane, Ryan G ORCID: https://orcid.org/0000-0002-7268-1744, Delgado, Nathan, John, Matthew P and Murphy, John A;-
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Item type: Article ID code: 55545 Dates: DateEvent2016Published3 March 2016Published Online8 February 2016AcceptedNotes: 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. Subjects: Science > Chemistry Department: Faculty of Science > Pure and Applied Chemistry Depositing user: Pure Administrator Date deposited: 16 Feb 2016 15:30 Last modified: 11 Nov 2024 11:19 URI: https://strathprints.strath.ac.uk/id/eprint/55545