Iron-Catalyzed Cross-Electrophile Coupling for the Formation of All-Carbon Quaternary Centers

Andria L. Pace, Felix Xu, Wei Liu, Marissa N. Lavagnino, David W.C. MacMillan

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

Quaternary carbon centers are desirable targets for drug discovery and complex molecule synthesis, yet the synthesis of these motifs within traditional cross-coupling paradigms remains a significant challenge due to competing β-hydride elimination pathways. In contrast, the bimolecular homolytic substitution (SH2) mechanism offers a unique and attractive alternative pathway. Metal porphyrin complexes have emerged as privileged catalysts owing to their ability to selectively form primary metal-alkyl complexes, thereby eliminating the challenges associated with tertiary alkyl complexation with a metal center. Herein, we report an iron-catalyzed cross-electrophile coupling of tertiary bromides and primary alkyl electrophiles for the formation of all-carbon quaternary centers through a biomimetic SH2 mechanism.

Original languageEnglish (US)
Pages (from-to)32925-32932
Number of pages8
JournalJournal of the American Chemical Society
Volume146
Issue number48
DOIs
StatePublished - Dec 4 2024

All Science Journal Classification (ASJC) codes

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry

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