title: 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).
authors.affiliation: Laboratoire de Chimie Moléculaire et Thioorganique, UMR CNRS 6507, INC3M FR3038, ENSICAEN & Université de Caen Basse-Normandie, 6 bvd Maréchal Juin, 14050 Caen, France. carole.witulski-alayrac@ensicaen.fr annie-claude.gaumont@ensicaen.fr.
authors.forename: Romain
authors.initials: R
authors.lastname: Veillard
authors.forename: Elise
authors.initials: E
authors.lastname: Bernoud
authors.forename: Ibrahim
authors.initials: I
authors.lastname: Abdellah
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Lohier
authors.forename: Carole
authors.initials: C
authors.lastname: Alayrac
authors.forename: Annie-Claude
authors.initials: AC
authors.lastname: Gaumont