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Issue 2, 2014
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Organic super-electron-donors: initiators in transition metal-free haloarene–arene coupling

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Abstract

Recent papers report transition metal-free couplings of haloarenes to arenes to form biaryls, triggered by alkali metal tert-butoxides in the presence of various additives. These reactions proceed through radical intermediates, but understanding the origin of the radicals has been problematic. Electron transfer from a complex formed from potassium tert-butoxide with additives, such as phenanthroline, has been suggested to initiate the radical process. However, our computational results encouraged us to search for alternatives. We report that heterocycle-derived organic electron donors achieve the coupling reactions and these donors can form in situ in the above cases. We show that an electron transfer route can operate either with phenanthrolines as additives or using pyridine as solvent, and we propose new heterocyclic structures for the respective electron donors involved in these cases. In the absence of additives, the coupling reactions are still successful, although more sluggish, and in those cases benzynes are proposed to play crucial roles in the initiation process.

Graphical abstract: Organic super-electron-donors: initiators in transition metal-free haloarene–arene coupling

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Supplementary files

Article information


Submitted
18 Aug 2013
Accepted
08 Oct 2013
First published
09 Oct 2013

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2014,5, 476-482
Article type
Edge Article

Organic super-electron-donors: initiators in transition metal-free haloarene–arene coupling

S. Zhou, G. M. Anderson, B. Mondal, E. Doni, V. Ironmonger, M. Kranz, T. Tuttle and J. A. Murphy, Chem. Sci., 2014, 5, 476
DOI: 10.1039/C3SC52315B

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