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Peer-reviewedCC BYOrganometallics

Ag(I)-Induced C-C Reductive Elimination from Pt(II): Role of Ag(I) and Counteranion.

  • Md Asmaul Hoque1
  • Zoë M Gehman1
  • Farzad Bastani2
  • Jonah G Clark3
  • Kevin P Quirion3
  • Aakashi Jain1
  • Diane A Dickie1
  • Amrit Venkatesh1
  • Petra Reinke2
  • Daniel H Ess3
  • T Brent Gunnoe1
  1. 1Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904, United States.
  2. 2Department of Materials Science and Engineering, University of Virginia, Charlottesville, Virginia 22904, United States.
  3. 3Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84604, United States.
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Abstract

Transition-metal-catalyzed C-C bond formation, including C-H functionalization reactions, often benefits from Lewis acid additives, among which Ag-(I) salts are widely used in Pd-catalyzed transformations. Despite this, direct experimental evidence defining the mechanistic role of Lewis acid additives remains limited. Herein, we investigate the role of Ag-(I) additives in C-C bond formation using (6-Fp)-PtPh2 (1) (6-Fp = 8,8'-(1,2-phenylene)-diquinoline) as the starting complex. The reaction of (6-Fp)-PtPh2 with different Ag-(I) compounds gives significantly different yields for the formation of biphenyl. Unexpectedly, our combined experimental, including 195Pt NMR spectroscopy and X-ray photoelectron spectroscopy, and computational studies reveal that Ag-(I) becomes incorporated into the Pt bonding framework to form multimetallic Pt/Ag intermediates that can promote reductive elimination. The Ag-(I) counteranion strongly influences the structure and reactivity of these intermediates, giving the rate trend AgTFA ≈ AgOTf > AgNO3 for the formation of biphenyl. These findings provide direct evidence for multimetallic cooperation involving Ag-(I) in C-C bond formation.

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Cite

BibTeXRIS
BibTeX
@article{hoque2026agiinduced,
  title = {{Ag(I)-Induced C-C Reductive Elimination from Pt(II): Role of Ag(I) and Counteranion.}},
  author = {Md Asmaul Hoque and Zoë M Gehman and Farzad Bastani and Jonah G Clark and Kevin P Quirion and Aakashi Jain and Diane A Dickie and Amrit Venkatesh and Petra Reinke and Daniel H Ess and T Brent Gunnoe},
  journal = {Organometallics},
  year = {2026},
  month = oct,
  doi = {10.1021/acs.organomet.6c00318},
  url = {https://europepmc.org/article/MED/42953812},
  note = {CC BY},
}
RIS
TY  - JOUR
TI  - Ag(I)-Induced C-C Reductive Elimination from Pt(II): Role of Ag(I) and Counteranion.
AU  - Md Asmaul Hoque
AU  - Zoë M Gehman
AU  - Farzad Bastani
AU  - Jonah G Clark
AU  - Kevin P Quirion
AU  - Aakashi Jain
AU  - Diane A Dickie
AU  - Amrit Venkatesh
AU  - Petra Reinke
AU  - Daniel H Ess
AU  - T Brent Gunnoe
PY  - 2026
DA  - 2026/10/15
JO  - Organometallics
DO  - 10.1021/acs.organomet.6c00318
UR  - https://europepmc.org/article/MED/42953812
AB  - Transition-metal-catalyzed C-C bond formation, including C-H functionalization reactions, often benefits from Lewis acid additives, among which Ag-(I) salts are widely used in Pd-catalyzed transformations. Despite this, direct experimental evidence defining the mechanistic role of Lewis acid additives remains limited. Herein, we investigate the role of Ag-(I) additives in C-C bond formation using (6-Fp)-PtPh2 (1) (6-Fp = 8,8'-(1,2-phenylene)-diquinoline) as the starting complex. The reaction of (6-Fp)-PtPh2 with different Ag-(I) compounds gives significantly different yields for the formation of biphenyl. Unexpectedly, our combined experimental, including 195Pt NMR spectroscopy and X-ray photoelectron spectroscopy, and computational studies reveal that Ag-(I) becomes incorporated into the Pt bonding framework to form multimetallic Pt/Ag intermediates that can promote reductive elimination. The Ag-(I) counteranion strongly influences the structure and reactivity of these intermediates, giving the rate trend AgTFA ≈ AgOTf > AgNO3 for the formation of biphenyl. These findings provide direct evidence for multimetallic cooperation involving Ag-(I) in C-C bond formation.
SN  - 0276-7333
SN  - 1520-6041
ER  -