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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
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Catalytic Dehydrogenative C-C Coupling by a Pincer-Ligated Iridium Complex.

Miles Wilklow-Marnell1, Bo Li2, Tian Zhou2

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Journal of the American Chemical Society
|June 9, 2017
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Pincer-iridium catalysts facilitate the dehydrogenative coupling of vinyl arenes to form diarylbutadienes. This reaction can proceed via disproportionation or with hydrogen acceptors, yielding up to 90% product.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Organic Synthesis

Background:

  • Vinyl arenes are versatile building blocks in organic synthesis.
  • Efficient catalytic methods for C-H functionalization are highly sought after.

Purpose of the Study:

  • To investigate the catalytic activity of pincer-iridium complexes in the dehydrogenative coupling of vinyl arenes.
  • To elucidate the reaction mechanism and explore substrate scope.

Main Methods:

  • Catalysis using pincer-iridium fragments (iPrPCP)Ir.
  • Density Functional Theory (DFT) calculations.
  • Synthesis and characterization of metalloindene intermediates.
  • Reactions with substituted styrenes.

Main Results:

  • Predominant formation of (E,E)-1,4-diaryl-1,3-butadienes via dehydrogenative coupling.
  • Yields up to 90% achieved through disproportionation or with sacrificial hydrogen acceptors.
  • Mechanism involves double C-H addition to form an iridium(III) metalloindene intermediate.
  • Demonstrated coupling of C(sp2)-H and C(sp3)-H bonds using 2,4,6-trimethylstyrene.

Conclusions:

  • Pincer-iridium complexes are effective catalysts for vinyl arene dehydrogenative coupling.
  • The reaction proceeds through a metalloindene intermediate.
  • The catalytic system is versatile and can couple various C-H bonds.