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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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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.