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Synthesis of Nixantphos Core-Functionalized Amphiphilic Nanoreactors and Application to Rhodium-Catalyzed Aqueous Biphasic 1-Octene Hydroformylation

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

Synthesis of Nixantphos Core-Functionalized Amphiphilic Nanoreactors and Application to Rhodium-Catalyzed Aqueous Biphasic 1-Octene Hydroformylation

Abstract

International audience; 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, France, Denmark, France
Subjects by Vocabulary

Microsoft Academic Graph classification: Convergent synthesis Styrene chemistry.chemical_compound Polymer chemistry Reversible addition−fragmentation chain-transfer polymerization Chain transfer Monomer chemistry Polymerization Ethylene glycol Hydroformylation

Library of Congress Subject Headings: lcsh:QD241-441 lcsh:Organic chemistry

Keywords

Polymers and Plastics, water-confined polymeric nanoreactors, Article, aqueous biphasic catalysis, hydroformylation, polymerization-induced self-assembly, RAFT polymerization, [CHIM.ORGA]Chemical Sciences/Organic chemistry, [CHIM.CATA]Chemical Sciences/Catalysis, General Chemistry, [CHIM.POLY]Chemical Sciences/Polymers, rhodium, nixantphos

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citations
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
12
Top 10%
Average
Top 10%
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EC| CCIMC
Project
CCIMC
Coordination chemistry inspires molecular catalysis
  • Funder: European Commission (EC)
  • Project Code: 860322
  • Funding stream: H2020 | MSCA-ITN-EJD
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