A phosphine-accelerated ArF-chloride bond activation process by palladium

Meital Orbach, Olena V. Zenkina, Yael Diskin-Posner, Mark A. Iron, Milko E. Van Der Boom

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)


We present a mechanistic study demonstrating selective Arf-Cl bond activation preceded by η2 coordination of Pd(PEt 3)2 to a C=C moiety of a partially fluorinated substrate. An intramolecular ring-walking process to activate the Arf-Cl bond is plausible, but an intermolecular reaction becomes dominant in the presence of PEt3. The latter pathway is significantly enhanced, since PEt 3 promotes dissociation of Pd(PEt3)3 from the C=C moiety followed by activation of the Arf-Cl bond. Our observations also show that PEt3 can be used to control reaction selectivity. The experimental observations are supported by density functional theory (DFT) calculations (at the SMD(toluene)-DSD-PBEP86/cc-pV(D+d)Z-PP//DF- PBE+dv2/SDD(d) level of theory).

Original languageEnglish
Pages (from-to)3074-3082
Number of pages9
Issue number10
Publication statusPublished - May 24 2013

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Fingerprint Dive into the research topics of 'A phosphine-accelerated Ar<sub>F</sub>-chloride bond activation process by palladium'. Together they form a unique fingerprint.

Cite this