Transformations of diphenylphosphinothioic acid tertiary amides mediated by directed ortho metallation |
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Authors: | el Hajjouji Hajar Belmonte Eva García-López Jesús Fernández Ignacio Iglesias María José Roces Laura García-Granda Santiago El Laghdach Anas López Ortiz Fernando |
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Affiliation: | área de Química Orgánica, Universidad de Almería, Carretera de Sacramento, 04120, Almería, Spain. |
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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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