Triple-Domino Synthesis of Tetrasubstituted Olefins

  • Author: ChemistryViews.org
  • Published: 09 April 2017
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
  • Source / Publisher: Advanced Synthesis & Catalysis/Wiley-VCH
thumbnail image: Triple-Domino Synthesis of Tetrasubstituted Olefins

The selective synthesis of tetrasubstituted olefins is still a challenge in organic synthesis. Paramasivan Thirumalai Perumala, CSIR-Central Leather Research Institute, Chennai, India, and colleagues have developed a palladium(0)-catalyzed triple domino process for the regio- and stereoselective synthesis of such olefins.


The team coupled 2-bromoaryl alkynyl biaryls or heteroaryls with norbornene using Pd(PPh3)4 as the catalyst and 1,4-dioxane as the solvent. The reaction involves the formation of three new C–C bonds (pictured red) through double carbopalladation and C–H activation to give a variety of congested tetrasubstituted olefins (example pictured) in good yields. A key step is the formation of a vinylic palladium(II) intermediate via a 5-exo-dig carbopalladation.


The method has a broad substrate scope and tolerates a wide range of substituents. Some of the products have a 9H-pyrrolo[1,2-a]indole core and can act as aggregation-induced emission (AIE) fluorophores.


 

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