Abstract
AbstractTreatment 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.
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