title: Identifying the roles of amino acids, alcohols and 1,2-diamines as mediators in coupling of haloarenes to arenes.
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.
authors.affiliation: WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde , 295 Cathedral Street, Glasgow G1 1XL, United Kingdom.
authors.forename: Shengze
authors.initials: S
authors.lastname: Zhou
authors.forename: Eswararao
authors.initials: E
authors.lastname: Doni
authors.forename: Greg M
authors.initials: GM
authors.lastname: Anderson
authors.forename: Ryan G
authors.initials: RG
authors.lastname: Kane
authors.forename: Scott W
authors.initials: SW
authors.lastname: MacDougall
authors.forename: Victoria M
authors.initials: VM
authors.lastname: Ironmonger
authors.forename: Tell
authors.initials: T
authors.lastname: Tuttle
authors.forename: John A
authors.initials: JA
authors.lastname: Murphy
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D003959:Diamines / Q000737:chemistry*; D006018:Glycols / Q000737:chemistry; D054879:Halogenation; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*
chemical_list: D000438:Alcohols; D000596:Amino Acids; D003959:Diamines; D006018:Glycols; D006841:Hydrocarbons, Aromatic