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Zhang X, Emge TJ, Ghosh R, et al. Selective cleavage of the C-C bonds of aminoethyl groups, via a multistep pathway, by a pincer iridium complex. J Am Chem Soc. 2005;127(23):8250-1doi: 10.1021/ja051300p.
Zhang, X., Emge, T. J., Ghosh, R., & Goldman, A. S. (2005). Selective cleavage of the C-C bonds of aminoethyl groups, via a multistep pathway, by a pincer iridium complex. Journal of the American Chemical Society, 127(23), 8250-1. https://doi.org/10.1021/ja051300p
Zhang, Xiawei, et al. "Selective cleavage of the C-C bonds of aminoethyl groups, via a multistep pathway, by a pincer iridium complex." Journal of the American Chemical Society vol. 127,23 (2005): 8250-1. doi: https://doi.org/10.1021/ja051300p
Zhang X, Emge TJ, Ghosh R, Goldman AS. Selective cleavage of the C-C bonds of aminoethyl groups, via a multistep pathway, by a pincer iridium complex. J Am Chem Soc. 2005 Jun 15;127(23):8250-1. doi: 10.1021/ja051300p. PMID: 15941235.
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J Am Chem Soc. 2005 Jun 15;127(23):8250-1. doi: 10.1021/ja051300p.

Selective cleavage of the C-C bonds of aminoethyl groups, via a multistep pathway, by a pincer iridium complex.

Journal of the American Chemical Society

Xiawei Zhang, Thomas J Emge, Rajshekhar Ghosh, Alan S Goldman

Affiliations

  1. Department of Chemistry, Rutgers, The State University of New Jersey, Piscataway, NJ 08854, USA.

PMID: 15941235 DOI: 10.1021/ja051300p

Abstract

A pincer-ligated iridium complex is found to react with N-ethylamines, HN(Et)R (R = cyclohexyl, tert-butyl, ethyl), to give the corresponding iridium isocyanide complexes (PCP)Ir(CH3)(H)(CNR) (PCP = kappa3-2,6-(tBu2PCH2)2C6H3). This novel, regioselective C-C bond cleavage reaction occurs readily under mild conditions (25-45 degrees C). The reaction is shown to proceed via initial dehydrogenation of the amine to give the corresponding imine (N-ethylidenealkylamine). The ethylidene sp2 C-H bond then undergoes addition to iridium, followed by methyl migration.

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