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el Hajjouji H, Belmonte E, García-López J, et al. Transformations of diphenylphosphinothioic acid tertiary amides mediated by directed ortho metallation. Org Biomol Chem. 2012;10(29):5647-58doi: 10.1039/c2ob25395j.
el Hajjouji, H., Belmonte, E., García-López, J., Fernández, I., Iglesias, M. J., Roces, L., García-Granda, S., El Laghdach, A., & López Ortiz, F. (2012). Transformations of diphenylphosphinothioic acid tertiary amides mediated by directed ortho metallation. Organic & biomolecular chemistry, 10(29), 5647-58. https://doi.org/10.1039/c2ob25395j
el Hajjouji, Hajar, et al. "Transformations of diphenylphosphinothioic acid tertiary amides mediated by directed ortho metallation." Organic & biomolecular chemistry vol. 10,29 (2012): 5647-58. doi: https://doi.org/10.1039/c2ob25395j
el Hajjouji H, Belmonte E, García-López J, Fernández I, Iglesias MJ, Roces L, García-Granda S, El Laghdach A, López Ortiz F. Transformations of diphenylphosphinothioic acid tertiary amides mediated by directed ortho metallation. Org Biomol Chem. 2012 Aug 07;10(29):5647-58. doi: 10.1039/c2ob25395j. Epub 2012 Jun 25. PMID: 22733007.
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Org Biomol Chem. 2012 Aug 07;10(29):5647-58. doi: 10.1039/c2ob25395j. Epub 2012 Jun 25.

Transformations of diphenylphosphinothioic acid tertiary amides mediated by directed ortho metallation.

Organic & biomolecular chemistry

Hajar el Hajjouji, Eva Belmonte, Jesús García-López, Ignacio Fernández, María José Iglesias, Laura Roces, Santiago García-Granda, Anas El Laghdach, Fernando López Ortiz

Affiliations

  1. Área de Química Orgánica, Universidad de Almería, Carretera de Sacramento, 04120, Almería, Spain.

PMID: 22733007 DOI: 10.1039/c2ob25395j

Abstract

ortho-Lithiation of N,N-diisopropyl-P,P-diphenylphosphinothioic amide using n-BuLi in the presence of TMEDA in diethyl ether followed by electrophilic trapping is described as an efficient method for the synthesis of ortho-functionalised derivatives in high yields. The structural modification of the phosphinothioic amide includes C-X (X = P, S, Si, Sn, I) and C-C bond forming reactions with a large variety of electrophiles. Additional applications based on functional group transformations are also reported. They include imine formation, desulfurization and Suzuki cross-coupling reactions on selected compounds.

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