Mechanistic Studies of Ligand Substitution, Linkage Isomerism, and Insertion Reactions in Electron Rich Pd(II) Complexes of a Zwitterionic Diimine Ligand

Feliciano-Carmona, Alberto; Wang, Xiqu; Hughes, Russell P.; Daugulis, Olafs; Brookhart, Maurice

doi:10.1021/acs.organomet.5c00011

Mechanistic Studies of Ligand Substitution, Linkage Isomerism, and Insertion Reactions in Electron Rich Pd(II) Complexes of a Zwitterionic Diimine Ligand

Journal Article · Mon May 12 04:00:00 EDT 2025 · Organometallics

DOI:https://doi.org/10.1021/acs.organomet.5c00011· OSTI ID:2566550

Feliciano-Carmona, Alberto ^[1]; Wang, Xiqu ^[1]; Hughes, Russell P. ^[2]; ^[1]; Brookhart, Maurice ^[1]

University of Houston, TX (United States)
Dartmouth College, Hanover, NH (United States)

We have prepared cationic palladium complexes possessing a new zwitterionic ligand bis-N,N’–1-(2,4,6-triphenylpyridyl) oxalamide [(N_^N)Pd(Me)(L)]⁺[BArF]^-, (BArF=3,5-(CF₃)₂C₆H₃, L=NCMe, CO). The structure of [(N_^N)Pd(Me)(CO)]⁺[BArF]^- was determined by X-ray diffraction analysis. Energy Decomposition Analysis (EDA) indi-cates this N_^N zwitterionic ligand is more electron-donating relative to bidentate diimine ligands. Low temperature NMR analysis shows the existence of linkage isomers with the N_^N isomer the most stable. Structures were assigned using NMR and DFT analysis. Barriers to interconversion of isomers are ΔG^‡ = 10-12 kcal/mol. Kinetics of acetoni-trile displacement from [(N_^N)Pd(Me)(NCCH₃)]⁺[BArF]^- by CD₃CN, ethylene and ^tBu₃P were measured and mechanisms of exchange determined. The ethylene complex, [(N_^N)Pd(Me)(C₂H₄)]⁺ was generated at -45 °C, and the barrier of migrato-ry insertion determined at 0 °C (ΔG^‡ = 23.4 kcal/mol) and compared to related diimine complexes. The methyl carbonyl complex undergoes migratory insertion in the presence of CO at -70 to -55 °C (ΔG^‡ = ca. 15.7 kcal/mol) to yield the acyl carbonyl complex. Furthermore, the neutral bis-trimethylsilylmethyl complex [(N_^N)Pd(CH₂SiMe₃)₂ was prepared and characterized by X-ray diffraction analysis. It displays dynamic behavior at very low temperatures in the NMR spectrum (-90 °C, ΔG^‡ =7.9 kcal/mol) which, supported by DFT analysis, is ascribed to rotation of the bulky -CH₂SiMe₃ groups.

View Accepted Manuscript (DOE)

Research Organization:: University of Houston, TX (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0024250

OSTI ID:: 2566550

Journal Information:: Organometallics, Journal Name: Organometallics Journal Issue: 10 Vol. 44; ISSN 0276-7333

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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