期刊
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
卷 -, 期 35, 页码 5854-5863出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejic.201200789
关键词
Click chemistry; Copper(I) catalysts; Aqueous media; 5-Iodotriazoles; 1-Iodoalkynes; Cycloaddition; Multicomponent reactions
资金
- Ministerio de Ciencia e Innovacion (MICINN) of Spain [CTQ2008-00506, RYC-2011-08451]
- Consolider Ingenio [CSD2007-00006]
- MICINN
- European Social Fund
- Scientific and Technical Services (UniOvi) X Ray Single Crystal Diffraction
Treatment of water-soluble phosphanes PTA (1) and DAPTA (2) with an equimolecular amount of azides (RO)(2)P(=S)N-3 (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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