Poly(4-dodecylstyrene) as a phase-selectively soluble polymer support in homogeneous catalysis

Khamatnurova, Tatyana; Bergbreiter, David E.

doi:10.1039/c2py20922e

Cited by 17 publications

(11 citation statements)

References 33 publications

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“…Many strategies have been reported for attaching 4‐DMAP covalently to polymeric structures in order to obtain recyclable, less toxic systems. This goal has been achieved mostly by polymer modifications . Only a few research groups have reported the preparation of catalytically active compounds based on a styrene‐type monomer .…”

Section: Introductionmentioning

confidence: 99%

Catalytic performance of methacrylate‐based poly‐4‐(dialkylamino)‐pyridines: activity prediction via NMR shifts

Mennenga

Menzel

Ritter

2016

Polymer International

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Section: Introductionmentioning

confidence: 99%

Catalytic performance of methacrylate‐based poly‐4‐(dialkylamino)‐pyridines: activity prediction via NMR shifts

Mennenga

Menzel

Ritter

2016

Polymer International

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“…This is an approach with considerable precedent at least for conventional phosphine ligands. 19,20 Results and discussion 16 Alternative strategies have also been used.…”

Section: Introductionmentioning

confidence: 99%

“…[19][20][21] The first 4-alkyl-substituted polystyrene support is an alternative to unsubstituted polystyrene. [19][20][21] The first 4-alkyl-substituted polystyrene support is an alternative to unsubstituted polystyrene.…”

Section: Introductionmentioning

confidence: 99%

“…19 A further consideration in our design of phase selectively soluble polyĲ4-alkylstyrene) supports for relatively lipophilic hindered phosphine ligands related to the fact that we have observed that the leaching of metals from soluble polymer supported catalysts is often higher in the first few cycles of a recycling study, especially when the mass of the catalyst or ligand is large relative to the mass of the support. Thus, we chose to use copolymers with a ca.…”

Section: Introductionmentioning

confidence: 99%

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Soluble polymer-supported hindered phosphine ligands for palladium-catalyzed aryl amination

Khamatnurova

Zhang

Suriboot

et al. 2015

Catal. Sci. Technol.

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Strategies for synthesis of more effective soluble supported ligands for phosphine-ligated Pd(0) cross coupling catalysts have been explored. Reversible addition-fragmentation chain transfer (RAFT) polymerization has been used to prepare alkane-soluble polyĲ4-alkylstyrene)-bound phosphine ligands. 4-tert-Butylstyrene and 4-dodecylstyrene were copolymerized with ca. 7 mol% of 4-chloromethylstyrene or a 4-diphenylphosphinestyrene monomer using RAFT chemistry to afford polyĲtert-butylstyrene-co-4dodecylstyrene) copolymers. Polymers with chloromethyl groups were allowed to react with the phenolic group of a hindered dicyclohexylbiarylphosphine ligand. This hindered polymer-bound phosphine formed reactive Pd complexes useful in haloarene amine couplings. All aryl halide amination reactions had Pd leaching that was typically <0.1% of the charged Pd with one example having only 0.02% Pd leaching. These Pd complexes of polyĲ4-alkylstyrene)-bound phosphines were also compared to similar hindered phosphine complexes formed with a polyisobutylene (PIB), whose terminus was also converted into a dicyclohexylbiarylphosphine ligand. Palladium catalysts ligated by these hindered biarylphosphines on polyĲ4-alkylstyrene) and PIB-bound both were recyclable in the absence of oxygen, had similar activity, and very low Pd leaching.

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“…Bergbreiter et al pioneered the use of polyethylene oligomers as soluble supports, chemistry that is currently experiencing resurgence in the literature . Numerous other types of polymer supports have been studied and most of them are typically recovered using either a solid/liquid or liquid/liquid technique …”

Section: Introductionmentioning

confidence: 99%

Use of an isotactic-propylene/hexene copolymer as a new, versatile, soluble support

Hicks

Lin

Osburn

et al. 2013

J. Polym. Sci. Part A: Polym. Chem.

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The use of isotactic‐poly(propylene‐co‐hexene) (iPPH) as new polymeric scaffold for synthesis as well as a phase‐selective, soluble polymer support for homogeneous catalysis is described. It was possible to functionalize olefin‐terminated iPPH using standard organic transformations. Each derivative could be isolated and purified using typical precipitations into a minimum amount of polar solvent, negating the need for wasteful work up and chromatographic procedures. Furthermore, it was demonstrated that an iPPH‐supported DMAP could serve as a recoverable, recyclable catalyst. Published 2013. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 600–605

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Poly(4-dodecylstyrene) as a phase-selectively soluble polymer support in homogeneous catalysis

Cited by 17 publications

References 33 publications

Catalytic performance of methacrylate‐based poly‐4‐(dialkylamino)‐pyridines: activity prediction via NMR shifts

Catalytic performance of methacrylate‐based poly‐4‐(dialkylamino)‐pyridines: activity prediction via NMR shifts

Soluble polymer-supported hindered phosphine ligands for palladium-catalyzed aryl amination

Use of an isotactic-propylene/hexene copolymer as a new, versatile, soluble support

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