Regioselective Cross-Electrophile Coupling of Epoxides and (Hetero)aryl Iodides via Ni/Ti/Photoredox Catalysis

Marvin Parasram, Benjamin J. Shields, Omar Ahmad, Thomas Knauber, Abigail G. Doyle

Research output: Contribution to journalArticlepeer-review

Abstract

A cross-electrophile coupling reaction of epoxides and (hetero)aryl iodides that operates via the merger of three catalytic cycles involving a Ni-, Ti-, and organic photoredox catalyst has been developed. Three distinct classes of epoxides, styrene oxides, cyclic epoxides, and terminal aliphatic epoxides, all undergo coupling in moderate to good yield and high regioselectivity with the use of three different nitrogen-based ligands for Ni under otherwise identical reaction conditions. The mild reaction conditions accommodate a broad scope of abundant and complex coupling partners. Mechanistic studies suggest that when styrene oxides are employed radical intermediates are involved via Ti-radical ring-opening of the epoxide. Conversely, for terminal aliphatic epoxides, involvement of an iodohydrin intermediate enables the formation of the unexpected linear product.

Original languageEnglish (US)
Pages (from-to)5821-5827
Number of pages7
JournalACS Catalysis
Volume10
Issue number10
DOIs
StatePublished - May 15 2020

Keywords

  • arylation
  • cross-electrophile coupling
  • epoxides
  • nickel catalysis
  • photochemistry
  • photoredox catalysis
  • radical chemistry
  • titanium catalysis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Fingerprint Dive into the research topics of 'Regioselective Cross-Electrophile Coupling of Epoxides and (Hetero)aryl Iodides via Ni/Ti/Photoredox Catalysis'. Together they form a unique fingerprint.

Cite this