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Decarbonylative ether dissection by iridium pincer complexes.

Changho Yoo1, Henry M Dodge1, Alexandra H Farquhar1

  • 1Department of Chemistry, University of North Carolina at Chapel Hill Chapel Hill North Carolina 27599-3290 USA ajmm@email.unc.edu.

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|June 14, 2021
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Summary
This summary is machine-generated.

Iridium complexes catalyze a novel ether transformation, breaking C-O bonds to yield hydrocarbyl units and carbon monoxide. This decarbonylation reaction offers a new pathway for ether functionalization.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Organic Synthesis

Background:

  • Ether functionalities are common in organic molecules but their selective cleavage can be challenging.
  • Iridium complexes are known for their catalytic activity in various transformations, including C-H activation and bond cleavage.

Purpose of the Study:

  • To report a unique chain-rupturing transformation of ethers mediated by iridium complexes.
  • To explore the scope and mechanism of this novel decarbonylation reaction.

Main Methods:

  • Synthesis and characterization of iridium(i) and iridium(iii) complexes supported by aminophenylphosphinite (NCOP) pincer ligands.
  • Investigation of intramolecular and intermolecular ether cleavage reactions.
  • Mechanistic studies involving key intermediate identification.

Main Results:

  • A novel iridium-catalyzed decarbonylation of ethers, converting C-O bonds into hydrocarbyl units and carbon monoxide.
  • Demonstration of intramolecular cleavage of macrocyclic and acyclic ethers.
  • Observation of intermolecular decarbonylation of cyclic and linear ethers using specific iridium complexes.
  • Elucidation of a mechanism involving iridium(i)-mediated double C-H bond activation.

Conclusions:

  • The reported transformation provides a new synthetic route for ether functionalization.
  • The catalytic system, utilizing iridium complexes with NCOP ligands, shows versatility in cleaving various ether types.
  • Mechanistic insights highlight the role of C-H activation in this unique decarbonylation process.