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Highly regioselective hydroformylation with hemispherical chelators.

David Sémeril1, Dominique Matt, Loïc Toupet

  • 1Laboratoire de Chimie Inorganique Moléculaire, Institut de Chimie UMR 7177, Université de Strasbourg, France. dsemeril@chimie.u-strasbg.fr

Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 8, 2008
PubMed
Summary

New hemispherical diphosphite ligands (L(R)) with C(2) symmetry were synthesized. These ligands, when complexed with rhodium, show high regioselectivity in hydroformylation reactions, producing predominantly linear aldehydes.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Supramolecular Chemistry

Background:

  • Calix[4]arenes are versatile macrocyclic platforms for designing ligands.
  • Rhodium-catalyzed hydroformylation is a crucial industrial process for aldehyde synthesis.
  • Achieving high regioselectivity (linear vs. branched products) remains a key challenge.

Purpose of the Study:

  • To synthesize novel hemispherical diphosphite ligands (L(R)) based on calix[4]arene scaffolds.
  • To investigate the catalytic activity and regioselectivity of rhodium complexes with these ligands in hydroformylation reactions.
  • To explore the influence of apical substituents on catalytic performance.

Main Methods:

  • Synthesis of C(2)-symmetric hemispherical diphosphite ligands (L(R)) from di-O-alkylated calix[4]arene precursors.
  • Formation of rhodium-chelate complexes using [Rh(acac)(CO)(2)] and the synthesized ligands.
  • Hydroformylation of various alkenes (octene, styrene, trans-2-octene, allyl benzyl ether) using the rhodium-ligand systems.

Main Results:

  • The L(R)/Rh systems efficiently form catalytic complexes with a well-defined molecular pocket.
  • Hydroformylation of octene with L(Pr)/Rh yielded a high linear-to-branched (l:b) aldehyde ratio of 58:1.
  • Replacing propyl groups with benzyl or naphthyl substituents further increased regioselectivity (l:b up to 100:1) by sterically influencing the catalytic site.
  • High linear aldehyde selectivity was also observed in the hydroformylation of styrene (up to 75%) and in tandem hydroformylation/amination reactions.

Conclusions:

  • Hemispherical diphosphite ligands derived from calix[4]arenes are effective in controlling regioselectivity in rhodium-catalyzed hydroformylation.
  • Apical substituents play a critical role in enhancing selectivity by sterically directing substrate approach to the catalytic center.
  • These ligands offer a promising avenue for developing highly selective catalysts for industrial aldehyde synthesis.