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synthesis of nixantphos core functionalized amphiphilic nanoreactors and application to rhodium catalyzed aqueous biphasic 1 octene hydroformylation

descriptionPublicationkeyboard_double_arrow_right Article 12 May 2020 France, Denmark, France, France Publisher:MDPI AGJournal:Polymers, volume 12, page 1,107 (eissn: 2073-4360,

Authors: Ahmad Joumaa; Florence Gayet; Eduardo J. Garcia-Suarez; Jonas Himmelstrup; Anders Riisager; Rinaldo Poli; Eric Manoury;

doi: 10.3390/polym12051107

pmid: 32408686

pmc: PMC7285327

synthesis of nixantphos core functionalized amphiphilic nanoreactors and application to rhodium catalyzed aqueous biphasic 1 octene hydroformylation

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Abstract

A latex of amphiphilic star polymer particles, functionalized in the hydrophobic core with nixantphos and containing P(MAA-co-PEOMA) linear chains in the hydrophilic shell (nixantphos-functionalized core-crosslinked micelles, or nixantphos@CCM), has been prepared in a one-pot three-step convergent synthesis using reversible addition-fragmentation chain transfer (RAFT) polymerization in water. The synthesis involves polymerization-induced self-assembly (PISA) in the second step and chain crosslinking with di(ethylene glycol) dimethacrylate (DEGDMA) in the final step. The core consists of a functionalized polystyrene, obtained by incorporation of a new nixantphos-functionalized styrene monomer (nixantphos-styrene), which is limited to 1 mol%. The nixantphos-styrene monomer was synthesized in one step by nucleophilic substitution of the chloride of 4-chloromethylstyrene by deprotonated nixantphos in DMF at 60 °C, without interference of either phosphine attack or self-induced styrene polymerization. The polymer particles, after loading with the [Rh(acac)(CO)2] precatalyst to yield Rh-nixantphos@CCM, function as catalytic nanoreactors under aqueous biphasic conditions for the hydroformylation of 1-octene to yield n-nonanal selectively, with no significant amounts of the branched product 2-methyl-octanal.

Countries

France, Denmark, France, France

Related Organizations

Université Paris Diderot
France
University of Toulouse
France
Technical University of Denmark
Laboratoire Parole et Langage
France
French National Centre for Scientific Research
France

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Keywords

RAFT polymerization, [CHIM.ORGA]Chemical Sciences/Organic chemistry, [CHIM.CATA]Chemical Sciences/Catalysis, water-confined polymeric nanoreactors, Nixantphos, Article, [CHIM.POLY]Chemical Sciences/Polymers, aqueous biphasic catalysis, Polymerization-induced self-assembly, Water-confined polymeric nanoreactors, rhodium, Hydroformylation, Rhodium, Aqueous biphasic catalysis, hydroformylation, polymerization-induced self-assembly, nixantphos

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synthesis of nixantphos core functionalized amphiphilic nanoreactors and application to rhodium catalyzed aqueous biphasic 1 octene hydroformylation

synthesis of nixantphos core functionalized amphiphilic nanoreactors and application to rhodium catalyzed aqueous biphasic 1 octene hydroformylation

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Synthesis and characterization of a large bite angle iridium nixantphos complex

Cation−π Interactions in the Benzylic Arylation of Toluenes with Bimetallic Catalysts

Cu(I) photosensitizers with alkylated diphosphines: Towards enhancing photostability and architecture extension

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