Nickel-Catalyzed Cross-Electrophile Coupling with Organic Reductants in Non-Amide Solvents

Lukiana L. Anka-Lufford, Kierra M.M. Huihui, Nicholas J. Gower, Laura K.G. Ackerman, Daniel J. Weix

Research output: Contribution to journalArticlepeer-review

40 Scopus citations

Abstract

Cross-electrophile coupling of aryl halides with alkyl halides has thus far been primarily conducted with stoichiometric metallic reductants in amide solvents. This report demonstrates that the use of tetrakis(dimethylamino)ethylene (TDAE) as an organic reductant enables the use of non-amide solvents, such as acetonitrile or propylene oxide, for the coupling of benzyl chlorides and alkyl iodides with aryl halides. Furthermore, these conditions work for several electron-poor heterocycles that are easily reduced by manganese. Finally, we demonstrate that TDAE addition can be used as a control element to ‘hold’ a reaction without diminishing yield or catalyst activity.

Original languageEnglish (US)
Pages (from-to)11564-11567
Number of pages4
JournalChemistry - A European Journal
Volume22
Issue number33
DOIs
StatePublished - 2016
Externally publishedYes

Keywords

  • cross-coupling
  • green chemistry
  • heterocycles
  • homogeneous catalysis
  • nickel

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Nickel-Catalyzed Cross-Electrophile Coupling with Organic Reductants in Non-Amide Solvents'. Together they form a unique fingerprint.

Cite this