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Ney JE, Wolfe JP. Synthesis and reactivity of azapalladacyclobutanes. J Am Chem Soc. 2006;128(48):15415-22doi: 10.1021/ja0660756.
Ney, J. E., & Wolfe, J. P. (2006). Synthesis and reactivity of azapalladacyclobutanes. Journal of the American Chemical Society, 128(48), 15415-22. https://doi.org/10.1021/ja0660756
Ney, Joshua E, and Wolfe, John P. "Synthesis and reactivity of azapalladacyclobutanes." Journal of the American Chemical Society vol. 128,48 (2006): 15415-22. doi: https://doi.org/10.1021/ja0660756
Ney JE, Wolfe JP. Synthesis and reactivity of azapalladacyclobutanes. J Am Chem Soc. 2006 Dec 06;128(48):15415-22. doi: 10.1021/ja0660756. PMID: 17132008.
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J Am Chem Soc. 2006 Dec 06;128(48):15415-22. doi: 10.1021/ja0660756.

Synthesis and reactivity of azapalladacyclobutanes.

Journal of the American Chemical Society

Joshua E Ney, John P Wolfe

Affiliations

  1. Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109-1055, USA.

PMID: 17132008 DOI: 10.1021/ja0660756

Abstract

N-Sulfonyl aziridines undergo oxidative addition to palladium(0) complexes generated in situ from mixtures of Pd2(dba)3 and 1,10-phenanthroline. The resulting azapalladacyclobutane complexes undergo intramolecular carbopalladation in the presence of copper(I) iodide to afford azapalladabicyclo[3.2.1]octanes. A deuterium-labeling experiment indicates that the oxidative addition proceeds via SN2-type attack of palladium(0) on the less-hindered carbon of the aziridine ring and that alkene insertion occurs in a syn fashion. The azapalladabicyclo[3.2.1]octane complexes undergo oxidative palladium-carbon bond functionalization in the presence of copper(II) bromide.

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