Cross-coupling and dehalogenation reactions catalyzed by (N-heterocyclic carbene)Pd(allyl)Cl complexes

O Navarro, H Kaur, P Mahjoor, Steven Patrick Nolan

Research output: Contribution to journalArticlepeer-review

337 Citations (Scopus)

Abstract

A series of well-defined, air- and moisture-stable (NHC)Pd(allyl)Cl (NHC = N-heterocyclic carbene) complexes has been used in several catalytic reactions: Suzuki-Miyaura cross-coupling, catalytic dehalogenation of aryl halides, and aryl amination. The scope of the three processes using various substrates was examined. A general system involving the use of (IPr)Pd(allyl)Cl as catalyst and (NaOBu)-Bu-t as base has proven to be highly active for the Suzuki-Miyaura cross-coupling of activated and unactivated aryl chlorides and bromides, for the catalytic dehalogenation of aryl chlorides, and for the catalytic aryl amination of aryl triflates. All reactions proceed in short reaction times and at mild temperatures. The system has also proven to be compatible with the microwave-assisted Suzuki-Miyaura cross-coupling and catalytic dehalogenation processes, affording yields similar to those of the conventionally heated analogous reactions.

Original languageEnglish
Pages (from-to)3173-3180
Number of pages8
JournalThe Journal of Organic Chemistry
Volume69
Issue number9
DOIs
Publication statusPublished - 30 Apr 2004

Keywords

  • N-HETEROCYCLIC CARBENE
  • PALLADIUM/IMIDAZOLIUM CHLORIDE SYSTEM
  • NITROGEN BOND FORMATION
  • ARYL CHLORIDES
  • GRIGNARD-REAGENTS
  • ROOM-TEMPERATURE
  • ORGANIC HALIDES
  • ORGANOBORON COMPOUNDS
  • (NHC)PD(ALLYL)CL NHC
  • ARYLBORONIC ACIDS

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