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).

Phosphine-substituted 1,2,3-triazoles as P,C- and P,N-ligands for photoluminescent coinage metal complexes

“…L PN was reported before by C. Alayrac and A.-C. Gaumond, but no further metal coordination has been carried out. 29 Following Pearson's concept of hard and soft acids and bases, 30,31 the nitrogen coordination site in L PN is suitable for the coordination of rather hard metals, whereas the phosphine prefers to coordinate to soft metals. Furthermore, the ligands L PC and L PN exhibit a rigid scaffold and a spatial proximity of their respective donor sites.…”

Azide Chemistry – An Inorganic Perspective, Part II[‡][3+2]‐Cycloaddition Reactions of Metal Azides and Related Systems

“…1,2,3-triazolyl-4-phosphines, formed from the borane complexes of phosphino-alkynes. [498] A variation of the copper-catalyzed Huisgen 1,3-dipolar cycloaddition involving a one-pot two-step transformation of trimethylsilyl-protected alkynes was used to prepare multidentate N-heterocyclic chelate ligands containing 1,2,3-triazole rings in high yields. [499] …”