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Carbonylative Transformations Using a DMAP-Based Pd-Catalyst through Ex Situ CO Generation.

Pallabi Halder1, Ashif Iqubal1, Krishanu Mondal1

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This summary is machine-generated.

A novel palladium complex enables phosphine-free aminocarbonylation and carbonylative Suzuki-Miyaura coupling. This efficient method uses chloroform as a carbon monoxide source for synthesizing valuable pharmaceutical compounds.

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Area of Science:

  • Organometallic Chemistry
  • Synthetic Organic Chemistry
  • Catalysis

Background:

  • Palladium-catalyzed carbonylative coupling reactions are crucial for synthesizing valuable organic compounds.
  • Traditional methods often require phosphine ligands and high pressures of carbon monoxide, posing safety and cost challenges.

Purpose of the Study:

  • To develop a novel, efficient, and phosphine-free protocol for aminocarbonylation and carbonylative Suzuki-Miyaura coupling.
  • To utilize a new palladium complex and a safe, inexpensive carbon monoxide source for these transformations.

Main Methods:

  • Synthesis and characterization of a novel palladium complex, [PdII(DMAP)2(OAc)2].
  • Application of the "Chloroform-COware" system for carbonylation using chloroform as a carbon monoxide surrogate.
  • Development of a COware-RB setup for sequential one-pot synthesis.

Main Results:

  • The novel palladium complex, [PdII(DMAP)2(OAc)2], effectively catalyzed aminocarbonylation and carbonylative Suzuki-Miyaura coupling with only 5 mol % loading.
  • Successful synthesis of pharmaceutically relevant compounds like CX-516, CX-546, and farampator.
  • Demonstrated sequential one-pot synthesis of indenoisoquinolines using the COware-RB setup.

Conclusions:

  • A phosphine-free, efficient, and safe catalytic system for carbonylative couplings has been established.
  • The developed methodology offers a cost-effective and practical approach for synthesizing complex molecules.
  • This protocol facilitates the synthesis of important pharmaceutical intermediates and drug candidates.