Identifying the roles of amino acids, alcohols and 1,2-diamines as mediators in coupling of haloarenes to arenes

Zhou, Shengze and Doni, Eswararao and Anderson, Greg M. and Kane, Ryan G. and MacDougall, Scott W. and Ironmonger, Victoria M. and Tuttle, Tell and Murphy, John A. (2014) Identifying the roles of amino acids, alcohols and 1,2-diamines as mediators in coupling of haloarenes to arenes. Journal of the American Chemical Society, 136 (51). pp. 17818-17826. ISSN 0002-7863

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      Abstract

      Coupling of haloarenes to arenes has been facilitated by a diverse range of organic additives in the presence of KO(t)Bu or NaO(t)Bu since the first report in 2008. Very recently, we showed that the reactivity of some of these additives (e.g., compounds 6 and 7) could be explained by the formation of organic electron donors in situ, but the role of other additives was not addressed. The simplest of these, alcohols, including 1,2-diols, 1,2-diamines, and amino acids are the most intriguing, and we now report experiments that support their roles as precursors of organic electron donors, underlining the importance of this mode of initiation in these coupling reactions.