4.5 Article

Nickel-Catalyzed Decarbonylative Coupling of Aryl Esters and Arylboronic Acids

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2015, Issue 25, Pages 5546-5553

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201500630

Keywords

Nickel; Biaryls; Esters; Cross-coupling; Decarbonylation

Funding

  1. University of British Columbia (UBC)
  2. Natural Sciences and Engineering Research Council of Canada (NSERC) Discovery
  3. Research Tools and Instrument (RTI) Grant Program
  4. Collaborative Research and Training Experience Program (CREATE) program

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A variety of functionalized biaryls can be accessed by coupling aryl and heteroaryl esters with boronic acids in Suzuki-Miyaura-type decarbonylative cross-coupling catalyzed by an affordable catalyst system composed of Ni(cod)(2) and PCy3. The methodology is tolerant of a variety of functional groups and presents an attractive alternative to the use of palladium catalysis currently used in industry to acquire such bis(hetero)aryls, but also reveals challenges associated with nickel catalysis of esters in cross-coupling chemistry.

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