Organic super-electron-donors : initiators in transition metal-free haloarene-arene coupling
Zhou, Sheng-Ze and Anderson, Greg M and Mondal, Bhaskar and Doni, Eswararao and Ironmonger, Vicki and Kranz, Michael and Tuttle, Tell and Murphy, J A (2014) Organic super-electron-donors : initiators in transition metal-free haloarene-arene coupling. Chemical Science, 5 (2). pp. 476-482. ISSN 2041-6539 (https://doi.org/10.1039/C3SC52315B)
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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, and with appropriate substrates, the coupling reactions are still successful although more sluggish,, and benzynes are proposed to play crucial roles in the initiation process in these cases.
ORCID iDs
Zhou, Sheng-Ze, Anderson, Greg M ORCID: https://orcid.org/0000-0001-7285-2745, Mondal, Bhaskar, Doni, Eswararao, Ironmonger, Vicki, Kranz, Michael, Tuttle, Tell and Murphy, J A;-
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Item type: Article ID code: 45301 Dates: DateEventFebruary 2014Published9 October 2013Published OnlineSubjects: Science > Chemistry Department: Faculty of Science > Pure and Applied Chemistry
Technology and Innovation Centre > BionanotechnologyDepositing user: Pure Administrator Date deposited: 22 Oct 2013 13:22 Last modified: 11 Nov 2024 10:31 Related URLs: URI: https://strathprints.strath.ac.uk/id/eprint/45301