Gold(I) Complexes with Ferrocenylphosphino Sulfonate Ligands: Synthesis and Application in the Catalytic Addition of Carboxylic Acids to Internal Alkynes in Water

被引:9
|
作者
Francos, Javier [1 ]
Esther Moreno-Narvaez, Maria [1 ]
Cadierno, Victorio [1 ]
Sierra, Diego [2 ]
Ariz, Katherine [2 ]
Gomez, Johana [3 ]
机构
[1] Univ Oviedo, Ctr Innovac Quim Avanzada ORFEO CINQA, IUQOEM,Fac Quim,Unidad Asociada CSIC, Dept Quim Organ & Inorgan,Lab Compuestos Organome, E-33006 Oviedo, Spain
[2] Univ Valparaiso, Fac Ciencias, Inst Quim & Bioquim, Lab Quim Organomet & Catalisis, Av Gran Bretana 1111, Valparaiso 2340000, Chile
[3] Pontificia Univ Catolica Valparaiso, NUcleo Biotecnol Curauma, Av Univ 330, Valparaiso 2340000, Chile
关键词
ferrocenylphosphines; gold catalysts; aqueous catalysis; enol esters; hydro-oxycarbonylation reactions; STEREOSELECTIVE ADDITION; GOLD(I)-CATALYZED ADDITION; ASYMMETRIC HYDROGENATION; CRYSTAL-STRUCTURE; ESTERS; ACCESS; HYDROCARBOXYLATION; ANNULATION; ALKENES; ARYL;
D O I
10.3390/catal9110955
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The synthesis and characterization of novel gold(I) complexes containing hydrophilic ferrocenylphosphino sulfonate ligands, i.e., compounds [AuCl{(eta(5)-C5H3PR2((SO3Pr)-Pr-i))Fe(eta(5)-C5H5)}] (R = Ph (2a), p-Tol (2b), Cy (2c)), are presented, including a single-crystal X-ray diffraction study on 2a. Complexes 2a-c were checked as catalysts for the intermolecular addition of carboxylic acids to nonactivated internal alkynes using water as a green reaction medium. The best results in terms of activity were obtained with 2a in combination with AgOAc, which was able to promote the selective anti addition of a variety of aromatic, aliphatic, and alpha,beta-unsaturated carboxylic acids to both symmetrical and unsymmetrical internal alkynes at 60 degrees C, employing metal loadings of only 2 mol %.
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页数:12
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