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Negishi cross-coupling reactions catalyzed by an aminophosphine-based nickel system: a reliable and general applicable reaction protocol for the high-yielding synthesis of biaryls.
Journal article

Negishi cross-coupling reactions catalyzed by an aminophosphine-based nickel system: a reliable and general applicable reaction protocol for the high-yielding synthesis of biaryls.

  • Gerber R Institute of Inorganic Chemistry, University of Zürich, Winterthurerstrasse 190, 8057 Zürich, Switzerland.
  • Frech CM
  • 2011-09-03
Published in:
  • Chemistry (Weinheim an der Bergstrasse, Germany). - 2011
English Treatment of NMP solutions of NiCl(2) with 1,1',1''-(phosphanetriyl)tripiperidine (≈2.05 equiv), dissolved in THF, in air at 25 °C forms a highly active catalytic system for the cross-coupling of a large variety of electronically activated, non-activated, deactivated, and ortho-substituted, heterocyclic, and functionalized aryl bromides and aryl chlorides with diarylzinc reagents. Very high levels of conversion and yields were obtained within 2 h at 60 °C in the presence of only 0.1 mol% of catalyst (based on nickel) and thus at catalyst loadings far lower than typically reported for nickel-catalyzed versions of the Negishi reaction. Various aryl halides-which may contain trifluoromethyl groups, fluorides, or other functional groups such as acetals, ketones, ethers, esters, lactones, amides, imines, anilines, alkenes, pyridines, quinolines, and pyrimidines-were successfully converted into the corresponding biaryls. Electronic and steric variations are tolerated in both reaction partners. Experimental observations indicate that a molecular (Ni(I)/Ni(III)) mechanism is operative.
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  • English
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https://sonar.rero.ch/global/documents/9113
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