Synthesis and Reactivity of Palladium(II) Alkyl Complexes that Contain Phosphine-cyclopentanesulfonate Ligands

Black, Rebecca E.; Jordan, Richard F.

doi:10.1021/acs.organomet.7b00572

Synthesis and Reactivity of Palladium(II) Alkyl Complexes that Contain Phosphine-cyclopentanesulfonate Ligands

Journal Article · Wed Aug 23 00:00:00 EDT 2017 · Organometallics

DOI:https://doi.org/10.1021/acs.organomet.7b00572· OSTI ID:1399121

Black, Rebecca E. ^[1]; ^[1]

Univ. of Chicago, IL (United States)

The synthesis of the phosphine-cyclopentanesulfonate pro-ligands Li/K[2-PPh₂-cyclopentanesulfonate] (Li/K[2a]), Li/K[2-P(2-OMe-Ph)₂-cyclopentanesulfonate] (Li/K[2b]), and H[2b], and the corresponding Pd(II) alkyl complexes (κ²-P,O-2a)PdMe(pyridine) (3a) and (κ²-P,O-2b)PdMe(pyridine) (3b) is described herein. The sulfonate-bridged base-free dimer {(2b)PdMe}₂ (4b) was synthesized by abstraction of pyridine from 3b using B(C₆F₅)₃. The borane-coordinated base-free dimer [{2b·B(C₆F₅)₃}PdMe]₂ (5b), in which B(C₆F₅)₃ binds to a sulfonate oxygen, was prepared by addition of 1 equiv of B(C₆F₅)₃ per Pd to 4b or addition of 2 equiv of B(C₆F₅)₃ to 3b. Compounds 3b, 4b, and 5b polymerize ethylene with low activity (up to 210 kg mol^–1 h^–1 at 250 psi and 80 °C) to linear polyethylene (M_n = 1950–5250 Da) with predominantly internal olefin placements. 3b and 4b copolymerize ethylene with methyl acrylate to linear copolymers that contain up to 11.7 mol % methyl acrylate, which is incorporated as –CH₂CH(CO₂Me)CH₂– (80%) in-chain units and –CH₂CH(CO₂Me)Me (8%) and –CH₂CH=CH(CO₂Me) (12%) chain-end units. 3b and 4b also copolymerize ethylene with vinyl fluoride to linear copolymers that contain up to 0.41 mol % vinyl fluoride, which is incorporated as –CH₂CHFCH₂– (~80%) in-chain units and –CH₂CF₂H (7%), –CH₂CHFCH₃ (5%), and –CH₂CH₂F (8%) chain-end units. Complexes 3b and 4b are more stable and active in ethylene polymerization than analogous (PAr₂-CH₂CH₂SO₃)PdR catalysts, but are less active than analogous (PAr₂-arenesulfonate)PdR catalysts. Low-temperature NMR studies show that 4b reacts with ethylene below -10 °C to form the ethylene adduct cis-P,R-(2b)PdMe(ethylene) (7b), which undergoes ethylene insertion at 5 °C. DFT calculations for a model (PMe₂-cyclopentanesulfonate)Pd(Pr)(ethylene) species show that ethylene insertion proceeds by cis-P,R/trans-P,R isomerization followed by migratory insertion, and that the lower activity of 3b and 4b vis-à-vis analogous (PAr₂-arenesulfonate)PdR catalysts results from a higher barrier for migratory insertion of the trans-P,R isomer.

View Accepted Manuscript (DOE)

Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS)

Sponsoring Organization:: National Science Foundation (NSF); US Department of Education; USDOE Office of Science (SC)

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 1399121

Journal Information:: Organometallics, Journal Name: Organometallics Journal Issue: 17 Vol. 36; ISSN 0276-7333

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: ENGLISH

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CCDC 1557506: Experimental Crystal Structure Determination Black, Rebecca E.; Jordan, Richard F. https://doi.org/10.5517/ccdc.csd.cc1p8q4t The current record is supplemented by this dataset	dataset	January 2017
CCDC 1557507: Experimental Crystal Structure Determination Black, Rebecca E.; Jordan, Richard F. https://doi.org/10.5517/ccdc.csd.cc1p8q5v The current record is supplemented by this dataset	dataset	January 2017
CCDC 1557508: Experimental Crystal Structure Determination Black, Rebecca E.; Jordan, Richard F. https://doi.org/10.5517/ccdc.csd.cc1p8q6w The current record is supplemented by this dataset	dataset	January 2017
CCDC 1557509: Experimental Crystal Structure Determination Black, Rebecca E.; Jordan, Richard F. https://doi.org/10.5517/ccdc.csd.cc1p8q7x The current record is supplemented by this dataset	dataset	January 2017

Synthesis and Reactivity of Palladium(II) Alkyl Complexes that Contain Phosphine-cyclopentanesulfonate Ligands

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