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Silyl alkynylphosphine-boranes: key precursors of triazolylphosphines via tandem desilylation-Click chemistry

Abstract : A versatile synthesis of 1,2,3-triazolyl-4-phosphines from the borane complexes of phosphino-alkynes is reported. The efficiency of the procedure relies on the use of readily available silyl-protected alkynylphosphine-boranes, which were subjected to desilylation with TBAF followed by copper-catalyzed azide–alkyne-cycloaddition in one pot. Subsequent treatment with DABCO afforded the targeted triazolylphosphines in high yields. The reported method was applied to the synthesis of the first example of an enantioenriched P-stereogenic triazolylphosphine (98.8% ee).A versatile synthesis of 1,2,3-triazolyl-4-phosphines from the borane complexes of phosphino-alkynes is reported. The efficiency of the procedure relies on the use of readily available silyl-protected alkynylphosphine-boranes, which were subjected to desilylation with TBAF followed by copper-catalyzed azide–alkyne-cycloaddition in one pot. Subsequent treatment with DABCO afforded the targeted triazolylphosphines in high yields. The reported method was applied to the synthesis of the first example of an enantioenriched P-stereogenic triazolylphosphine (98.8% ee).
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https://hal-normandie-univ.archives-ouvertes.fr/hal-01848078
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Submitted on : Tuesday, July 24, 2018 - 11:49:11 AM
Last modification on : Thursday, July 2, 2020 - 3:21:39 AM

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Romain Veillard, Elise Bernoud, Ibrahim Abdellah, Jean-François Lohier, Carole Alayrac, et al.. Silyl alkynylphosphine-boranes: key precursors of triazolylphosphines via tandem desilylation-Click chemistry. Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2014, 12, pp.3635-3640. ⟨10.1039/C4OB00397G⟩. ⟨hal-01848078⟩

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