The Manganese-Catalyzed Cross-Coupling Reaction and the Influence of Trace Metals

Carola Santilli, Somayyeh Sarvi Beigbaghlou, Andreas Ahlburg, Giuseppe Antonacci, Peter Fristrup, Per-Ola Norrby, Robert Madsen

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Abstract

The substrate scope of the MnCl2-catalyzed cross-coupling between aryl halides and Grignard reagents has been extended to several methyl-substituted aryl iodides by performing the reaction at elevated temperature in a microwave oven. A radical clock experiment revealed the presence of an aryl radical as an intermediate leading to the proposal of an SRN1 pathway for the coupling. The mechanistic information gave rise to suspicion about two previously published cross-coupling reactions catalyzed by manganese(II) salts. As a result, the coupling between aryl halides and organostannanes as well as between aryl halides and amines were revisited. Both reactions were found impossible to reproduce without the addition of small amounts of palladium or copper and are therefore not believed to be catalyzed by manganese.
Original languageEnglish
JournalEuropean Journal of Organic Chemistry
Volume2017
Issue number35
Pages (from-to)5269-5274
ISSN1434-193X
DOIs
Publication statusPublished - 2017

Keywords

  • Earth-abundant metals
  • Cross-coupling
  • Grignard reagent
  • Manganese
  • Radical reactions
  • Trace analysis

Cite this

Santilli, C., Beigbaghlou, S. S., Ahlburg, A., Antonacci, G., Fristrup, P., Norrby, P-O., & Madsen, R. (2017). The Manganese-Catalyzed Cross-Coupling Reaction and the Influence of Trace Metals. European Journal of Organic Chemistry, 2017(35), 5269-5274. https://doi.org/10.1002/ejoc.201701005