N-Methylcaprolactam as a Dipolar Aprotic Solvent for Iron-Catalyzed Cross-Coupling Reactions: Matching Efficiency with Safer Reaction Media

Elwira Bisz, Pamela Podchorodecka, Michal Szostak

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

Although iron-catalysis provides a powerful alternative to the more conventional palladium and nickel in the cross-coupling arena, the major limitation is the necessity for carcinogenic N-methylpyrrolidone as a co-solvent in the vast majority of catalytic reactions. Herein, we introduce N-methylcaprolactam as an efficient, non-toxic and practical dipolar aprotic solvent for iron-catalyzed C(sp 2 )−C(sp 3 ) alkylative cross-coupling of aryl chlorides and tosylates. The utility of this method is reflected by its wide substrate scope, high yields and capacity to cross-couple challenging alkyl organometallics prone to b-hydride elimination and homocoupling. Considering the broad utility of iron-catalyzed cross-coupling, we envision that N-methylcaprolactam will find wide application as a substitute for carcinogenic NMP.

Original languageEnglish (US)
Pages (from-to)1196-1199
Number of pages4
JournalChemCatChem
Volume11
Issue number4
DOIs
StatePublished - Feb 20 2019

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Keywords

  • catalysis
  • cross-coupling
  • green solvents
  • iron catalysis
  • sustainability

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