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Ruthenium(II)-Mediated Carbon-Carbon Bond Formation between Acetonitrile and Pyrrole: Combined Experimental and Computational Study

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This article discusses ruthenium(II)-mediated carbon-carbon bond formation between acetonitrile and pyrrole.

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10 p.

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Pittard, Karl A.; Cundari, Thomas R., 1964-; Gunnoe, T. Brent; Day, Cynthia S. & Petersen, Jeffrey L. September 13, 2005.

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This article discusses ruthenium(II)-mediated carbon-carbon bond formation between acetonitrile and pyrrole.

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10 p.

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Reprinted with permission from Organometallics. Copyright 2005 American Chemical Society.

Abstract: The reaction of TpRu(CO)(NCMe)(Me) (1) and pyrrole forms TpRu(CO) {κ2-N,N-(H)N = C(Me)(NC4H3)} (2). The formation of complex 2 involves the cleavage of the N-H bond and 2-position C-H bonds of pyrrole as well as a C-C bond forming step between pyrrole and the acetonitrile ligand of 1. Mechanistic studies indicate that the most likely reaction pathway involves initial metal-mediated N-H activation of pyrrole to produce TpRu(CO)(N-pyrrolyl)-(NCMe) (3) followed by C-C bond formation and proton transfer. Complex 3 has been independently prepared and demonstrated to convert to 2. Computational studies support the suggested selectivity for initial N-H bond cleavage in preference to C-H bond activation.

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  • Organometallics, 2005, Washington D.C.: American Chemical Society, pp. 5015-5024

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  • Publication Title: Organometallics
  • Volume: 24
  • Page Start: 5015
  • Page End: 5024
  • Pages: 10
  • Peer Reviewed: Yes

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  • September 13, 2005

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  • March 9, 2012, 2:17 p.m.

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  • Jan. 9, 2015, 3:37 p.m.

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Pittard, Karl A.; Cundari, Thomas R., 1964-; Gunnoe, T. Brent; Day, Cynthia S. & Petersen, Jeffrey L. Ruthenium(II)-Mediated Carbon-Carbon Bond Formation between Acetonitrile and Pyrrole: Combined Experimental and Computational Study, article, September 13, 2005; [Washington, D.C.]. (https://digital.library.unt.edu/ark:/67531/metadc77184/: accessed February 19, 2025), University of North Texas Libraries, UNT Digital Library, https://digital.library.unt.edu; crediting UNT College of Arts and Sciences.

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