Hybrid super electron donors - preparation and reactivity

Jean Garnier, Douglas William THOMSON, Sheng-Ze Zhou, Phillip I Jolly, Leonard E A Berlouis, John A Murphy

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

Neutral organic electron donors, featuring pyridinylidene–imidazolylidene, pyridinylidene–benzimidazolylidene and imidazolylidene–benzimidazolylidene linkages are reported. The pyridinylidene–benzimidazolylidene and imidazolylidene–benzimidazolylidene hybrid systems were designed to be the first super electron donors to convert iodoarenes to aryl radicals at room temperature, and indeed both show evidence for significant aryl radical formation at room temperature. The stronger pyridinylidene–imidazolylidene donor converts iodoarenes to aryl anions efficiently under appropriate conditions (3 equiv of donor). The presence of excess sodium hydride base has a very important and selective effect on some of these electron-transfer reactions, and a rationale for this is proposed
Original languageEnglish
Pages (from-to)994-1002
Number of pages9
JournalBeilstein Journal of Organic Chemistry
Volume8
DOIs
Publication statusPublished - 2012

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Keywords

  • aryl iodide
  • electron transfer
  • hybrid donors
  • reduction

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