Novel Phosphinite and Phosphonite Copper(I) Complexes: Efficient Catalysts for Click Azide-Alkyne Cycloaddition Reactions

被引:51
作者
Lal, Steven [1 ]
McNally, Jayne [1 ]
White, Andrew J. P. [1 ]
Diez-Gonzalez, Silvia [1 ]
机构
[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England
基金
英国工程与自然科学研究理事会;
关键词
M4X4; CORE; MOLECULAR-STRUCTURE; CONJUGATE ADDITION; LIGANDS; CHEMISTRY; DIETHYLZINC; SILVER(I); CRYSTAL;
D O I
10.1021/om200791u
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The preparation of novel phosphinite- and phosphonite-bearing copper(I) complexes of the general formula [CuX(L)] is reported. These compounds, which remain scarce in the literature, could be prepared using readily available starting materials and were spectroscopically and structurally characterized. These complexes, together with their known phosphine and phosphite analogues, were then applied to the 1,3-dipolar cycloaddition of azides and alkynes, to find that the new complexes displayed the best activities. Full optimization of the reaction conditions resulted in a noteworthy Click catalytic system, active under very mild reaction conditions in the absence of any additive and using low metal loadings.
引用
收藏
页码:6225 / 6232
页数:8
相关论文
共 51 条
[31]   Cu-catalyzed azide-alkyne cycloaddition [J].
Meldal, Morten ;
Tornoe, Christian Wenzel .
CHEMICAL REVIEWS, 2008, 108 (08) :2952-3015
[32]   Cage Phosphinites: Ligands for Efficient Nickel-Catalyzed Hydrocyanation of 3-Pentenenitrile [J].
Mikhel, Igor S. ;
Garland, Michael ;
Hopewell, Jonathan ;
Mastroianni, Sergio ;
McMullin, Claire L. ;
Orpen, A. Guy ;
Pringle, Paul G. .
ORGANOMETALLICS, 2011, 30 (05) :974-985
[33]   Copper-Catalyzed Tandem [2,3]-Rearrangement and 6π-3-Azatriene Electrocyclization in (E)-O-Propargylic α,β-Unsaturated Oximes [J].
Nakamura, Itaru ;
Zhang, Dong ;
Terada, Masahiro .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (23) :7884-+
[35]   A Highly Active Catalyst for Huisgen 1,3-Dipolar Cycloadditions Based on the Tris(triazolyl)methanol-Cu(I) Structure [J].
Oezcubukcu, Salih ;
Ozkal, Erhan ;
Jimeno, Ciril ;
Pericas, Miquel A. .
ORGANIC LETTERS, 2009, 11 (20) :4680-4683
[36]  
Orio A.A., 1969, INORG CHIM ACTA, V3, P8
[37]  
Owsley D.C., 1972, Org. Syn, V52, P128
[38]   Multivalent neoglycoconjugates by regiospecific cycloaddition of alkynes and azides using organic-soluble copper catalysts [J].
Pérez-Balderas, F ;
Ortega-Muñoz, M ;
Morales-Sanfrutos, J ;
Hernández-Mateo, F ;
Calvo-Flores, FG ;
Calvo-Asín, JA ;
Isac-García, J ;
Santoyo-González, F .
ORGANIC LETTERS, 2003, 5 (11) :1951-1954
[39]  
Pryjomska I, 2006, DALTON T, P213, DOI 10.1039/b512835h
[40]   Thioether-functionalized ferrocenyl-bis(phosphonite), Fe{(C5H4)P(-OC10H6(μ-S)C10H6O-)}2:: Synthesis, coordination behavior, and application in suzuki-miyaura cross-coupling reactions [J].
Punji, Benudhar ;
Mague, Joel T. ;
Balakrishna, Maravanji S. .
INORGANIC CHEMISTRY, 2007, 46 (24) :10268-10275