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

Tools

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

[thumbnail of Barham_etal_AC2016_double_deprotonation_of_pyridinols_generates_potent_organic_electron_donor]
Preview
 Text. Filename: Barham_etal_AC2016_double_deprotonation_of_pyridinols_generates_potent_organic_electron_donor.pdf
Accepted Author Manuscript
Download (1MB)| Preview

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 logoORCID: https://orcid.org/0000-0003-1675-9399, Coulthard, Graeme ORCID logoORCID: https://orcid.org/0000-0002-4413-2828, Kane, Ryan G ORCID logoORCID: https://orcid.org/0000-0002-7268-1744, Delgado, Nathan, John, Matthew P and Murphy, John A;
  • Item type:Article
    ID code:55545
    Dates:
    Date
    Event
    2016
    Published
    3 March 2016
    Published Online
    8 February 2016
    Accepted
    Notes: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:12 Dec 2024 03:58
    URI:https://strathprints.strath.ac.uk/id/eprint/55545
CORE (COnnecting REpositories)