Arylpalladium Phosphonate Complexes as Reactive Intermediates in Phosphorus-Carbon Bond Forming Reactions

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Article discussing research on arylpalladium phosphonate complexes as reactive intermediates in phosphorus-carbon bond forming reactions.

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9 p.

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Kohler, Mark C.; Grimes, Thomas V.; Wang, Xiaoping; Cundari, Thomas R., 1964- & Stockland, Robert A., Jr. January 21, 2009.

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Article discussing research on arylpalladium phosphonate complexes as reactive intermediates in phosphorus-carbon bond forming reactions.

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9 p.

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Reprinted with permission from Organometallics. Copyright 2009 American Chemical Society.

Abstract: Phosphorus-carbon bond formation from discrete transition metal complexes have been investigated through a combination of synthetic, spectroscopic, crystallographic, and computational methods. Reactive intermediates of the type (diphosphine)Pd(aryl)P(O)(OEt)2) have been prepared, characterized, and studied as possible intermediates in metal-mediated coupling reactions. Several of the reactive intermediates were characterized crystallographically, and a discussion of the solid state structures is presented. In contrast to other carbon-heteroelement bond forming reactions, palladium complexes containing electron-donating substituents on the aromatic fragment exhibited faster rates of reductive elimination. Large bit angle diphosphine ligands induced rapid rates of elimination, while bipyridine and small bite angle diphosphine ligands resulted in much slower rates of elimination. An investigation of the effect of typical impurities on the elimination reaction was carried out. While excess diphosphine, pyridine, and acetonitrile had little effect on the observed rate, the addition of water slowed the phosphorus-carbon bond forming reaction. Coordination of water to the complex was observed spectroscopically and crystallographically. Computational studies were utilized to probe the reaction pathways for P-C bond formation via Pd catalysis.

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  • Organometallics, 2009, Washington D.C.: American Chemical Society, pp. 1193-1201

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  • Publication Title: Organometallics
  • Volume: 28
  • Page Start: 1193
  • Page End: 1201
  • Pages: 9
  • Peer Reviewed: Yes

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The Scholarly Works Collection is home to materials from the University of North Texas community's research, creative, and scholarly activities and serves as UNT's Open Access Repository. It brings together articles, papers, artwork, music, research data, reports, presentations, and other scholarly and creative products representing the expertise in our university community. Access to some items in this collection may be restricted.

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  • January 21, 2009

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  • March 9, 2012, 2:17 p.m.

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  • Jan. 9, 2015, 5:07 p.m.

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Kohler, Mark C.; Grimes, Thomas V.; Wang, Xiaoping; Cundari, Thomas R., 1964- & Stockland, Robert A., Jr. Arylpalladium Phosphonate Complexes as Reactive Intermediates in Phosphorus-Carbon Bond Forming Reactions, article, January 21, 2009; [Washington, D.C.]. (digital.library.unt.edu/ark:/67531/metadc77191/: accessed May 25, 2017), University of North Texas Libraries, Digital Library, digital.library.unt.edu; crediting UNT College of Arts and Sciences.