Cycloaurated phosphinothioic amide complex as a precursor of gold(I) nanoparticles: Efficient catalysts for A3 synthesis of propargylamines under solvent-free conditions
| Autor: | Santiago García-Granda, Laura Roces, Hajar el Hajjouji, Eva Belmonte Sánchez, Esteban P. Urriolabeitia, Pedro Villuendas, María José Iglesias, Fernando López Ortiz |
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| Přispěvatelé: | European Commission, Ministerio de Ciencia e Innovación (España), Ministerio de Economía y Competitividad (España), Gobierno de Aragón |
| Rok vydání: | 2017 |
| Předmět: |
010405 organic chemistry
Organic Chemistry chemistry.chemical_element Nanoparticle 010402 general chemistry Photochemistry 01 natural sciences 0104 chemical sciences Catalysis Inorganic Chemistry chemistry.chemical_compound Transmetalation chemistry Amide Polymer chemistry Moiety Physical and Theoretical Chemistry Tin Pincer ligand Derivative (chemistry) |
| Zdroj: | Digital.CSIC. Repositorio Institucional del CSIC instname |
| ISSN: | 1520-6041 0276-7333 |
| Popis: | A C,S-cycloaurated complex based on an ortho-substituted phosphinothioic amide framework has been synthesized in high yield through tin(IV)-Au(III) transmetalation from the corresponding chlorodimethylstannyl derivative. The latter was prepared in a two-step process involving directed ortho lithiation/quenching with MeSnCl followed by Me/Cl exchange. The tin(IV) and gold(III) complexes have been characterized in solution and in the solid state. In both complexes, the phosphinothioic amide moiety acts as a C-C-P-S pincer ligand with formation of five-membered-ring metalacycles. The use of the gold(III) complex in the amine-aldehyde-alkyne (A) three-component coupling synthesis of propargylamines showed that the compound is transformed into the Sonogashira-type o-alkynylphosphinothioic amide with generation of Au(I) nanoparticles with an average size of around 7 nm. These nanoparticles proved to be excellent catalysts in A coupling processes, providing propargylamines in high yields under solvent-free conditions with loadings as low as 0.1 mol % and without the use of additives. We thank the MINECO and FEDER program for financial support (projects CTQ2011-27705 and CTQ2014-57157-P). E.B.S. thanks the MICINN for a Ph.D. fellowship. E.P.U. thanks the Gobierno de Aragon-FEDER (Spain, group E97) for financial support. |
| Databáze: | OpenAIRE |
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