Reductive elimination from arylpalladium cyanide complexes.

Journal of the American Chemical Society
Jessica L Klinkenberg, John F Hartwig

Abstract

We report the isolation and characterization of arylpalladium cyanide complexes that undergo reductive elimination to form arylnitriles. The rates of reductive elimination from a series of arylpalladium cyanide complexes reveal that the electronic effects on the reductive elimination from arylpalladium cyanide complexes are distinct from those on reductive reductive eliminations from arylpalladium alkoxo, amido, thiolate, and enolate complexes. Arylpalladium cyanide complexes containing aryl ligands with electron-donating substituents undergo reductive elimination of aromatic nitriles faster than complexes containing aryl ligands with electron-withdrawing substituents. In addition, the transition state for the reductive elimination of the aromatic nitrile is much different from that for reductive eliminations that occur from most other arylpalladium complexes. Computational studies indicate that the reductive elimination of an arylnitrile from Pd(II) occurs through a transition state more closely related in structure and electronic distribution to that for the insertion of CO into a palladium-aryl bond.

References

Aug 9, 2002·Journal of the American Chemical Society·Juventino J GarciaWilliam D Jones
Apr 17, 2003·Chemistry : a European Journal·Mark SundermeierMatthias Beller

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Citations

Jul 21, 2017·Journal of the American Chemical Society·Zhen LiuKeary M Engle
Oct 6, 2018·Organic & Biomolecular Chemistry·Zhouen ZhangTakamitsu Hosoya
Jul 2, 2015·Angewandte Chemie·Masashi ShigenobuHiroaki Sasai
Jul 11, 2020·Angewandte Chemie·Alexandre GenouxCristina Nevado
Aug 13, 2013·Angewandte Chemie·Todd D SenecalStephen L Buchwald
Aug 12, 2017·Angewandte Chemie·Sukdev BagDebabrata Maiti
Jan 3, 2015·Organic Letters·Daniel T Cohen, Stephen L Buchwald
Oct 28, 2017·Journal of the American Chemical Society·Sophie I Arlow, John F Hartwig

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