Active and Recyclable Polyethylene‐Supported Iridium‐(N‐ Heterocyclic Carbene) Catalyst for Hydrogen/Deuterium Exchange Reactions

Abstract

Them ultistep synthesiso fapolyethylenesupported iridium(III)-(N-heterocyclic carbene) hydrogen/deuterium exchangec atalyst was performed starting from an iodo-polyethylene obtained via catalyzed polyethylene chain growth( CCG) on magnesium. Unique thermomorphicp olyethylene properties give the possibility to perform catalytic hydrogen/ deuterium exchanger eactions at 100 8 8Ci nt he homogeneousp hase with simplec atalyst separation as ap recipitate at room temperature.T he catalytic ac-tivity of the polymer-supportedc atalyst was compared with that of its monomeric analogue.T he catalytic studies showedt hat the supported catalyst exhibits similar profiles and turnovern umbersa sh omogeneous counterparts without deactivation.

Reusable N-Heterocyclic Carbene Complex Catalysts and Beyond: A Perspective on Recycling Strategies

“…Recently in 2016, Thieuleux et al reported a polyethylene (PE)-supported NHC-Ir catalyst (282) through solid phase synthesis (Scheme 127). 329 Iodo-end-capped polyethylene (PE-I) and mesitylimidazole were refluxed in toluene to afford polyethylene-supported mesitylimidazolium (PE-MesIm). This was followed by reaction with Ag 2 O to provide the PE-supported NHC-Ag complex, and finally, the target PE-supported NHC-Ir catalyst 282 was obtained through a transmetalation process.…”

The Pivotal Role of Catalysis in France: Selected Examples of Recent Advances and Future Prospects.

“…Either soluble catalysts precipitate without prior modification (for example, multi‐charged polyoxometalates) or they need to be immobilized on structures like polymers or dendrimers whose separation through precipitation is more efficient. Examples of thermomorphic catalysts recently developed by French teams include the anchoring of an iridium carbene [(NHC)IrCp*Cl 2 ] on polyethylene, which is soluble in hot polar solvent and insoluble upon cooling. The resulting entity was shown to be effective for catalytic hydrogen/deuterium exchanges in organic compounds targeted for in vivo studies.…”

A Thermomorphic Polyethylene‐Supported Imidazolium Salt for the Fixation of CO2 into Cyclic Carbonates

“…reported a ruthenium‐based catalyst supported on PE for the olefin ring‐closing metathesis and Boisson, Thieuleux et al . described an iridium‐based catalyst grafted on PE for the D/H exchange . To the best of our knowledge, end‐functionalized thermomorphic PE has never been used as support for organocatalysts.…”