1418001-42-9Relevant articles and documents
(Iminophosphorane)copper(I) complexes as highly efficient catalysts for 1,3-dipolar cycloaddition of azides with terminal and 1-iodoalkynes in water: One-pot multi-component reaction from alkynes and in situ generated azides
Garcia-Alvarez, Joaquin,Diez, Josefina,Gimeno, Jose,Suarez, Francisco J.,Vincent, Cristian
, p. 5854 - 5863 (2012)
Treatment of water-soluble phosphanes PTA (1) and DAPTA (2) with an equimolecular amount of azides (RO)2P(=S)N3 (R = Et, Ph) leads to high-yield formation of the N-thiophosphorylated iminophosphorane derivatives 3b and 4a,b, respectively. The reaction of these new iminophosphorane ligands with [Cu(NCCH3)4][PF6] (in a 2:1 molar ratio) has been investigated. The resulting (iminophosphorane)copper(I) complexes 5b and 6a,b are efficient catalysts for the three-component cycloaddition reaction (organic halide, NaN3 and terminal alkynes) in aqueous media to afford regioselectively, under mild and aerobic conditions according to click laws , 1,4-disubstituted triazoles with a broad substrate scope and functional compatibility. The unprecedented application of the analogous (iminophosphorane)copper(I) catalyst 5a to a one-pot three-component reaction with 1-iodoalkynes as an internal alkyne in aqueous medium is also reported. ESI-MS analysis of 5a in water and DFT theoretical calculations [B3LYP/6-31G(d)] have been carried out providing valuable insight into the actual active species responsible for catalytic activity in water. A new family of CuI complexes exhibit versatile and efficient catalytic activity in Huisgen cycloadditions of azides and 1-iodoalkynes in aqueous media under mild conditions; these are the first well-defined CuI catalysts found to be active in a three-component reaction with 1-iodoalkynes in aerobic aqueous conditions. Copyright
