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

Shengze Zhou, Eswararao Doni, Greg M. Anderson, Ryan G. Kane, Scott W. MacDougall, Victoria M. Ironmonger, Tell Tuttle, John A. Murphy

Research output: Contribution to journalArticle

79 Citations (Scopus)
175 Downloads (Pure)

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.
Original languageEnglish
Pages (from-to)17818-17826
Number of pages9
JournalJournal of the American Chemical Society
Volume136
Issue number51
Early online date4 Dec 2014
DOIs
Publication statusPublished - 24 Dec 2014

Keywords

  • organic electron donors
  • organic additives
  • haloarenes
  • arenes

Fingerprint Dive into the research topics of 'Identifying the roles of amino acids, alcohols and 1,2-diamines as mediators in coupling of haloarenes to arenes'. Together they form a unique fingerprint.

  • Projects

  • Cite this