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Cycloaurated phosphinothioic amide complex as a precursor of gold(I) nanoparticles: Efficient catalysts for A3 synthesis of propargylamines under solvent-free conditions

AuthorsBelmonte Sánchez, Eva; Iglesias, María José; Hajjouji, Hajjouji el; Roces, Laura; García-Granda, Santiago ; Villuendas, Pedro ; Urriolabeitia, Esteban P.
Issue Date2017
PublisherAmerican Chemical Society
CitationOrganometallics 36(10): 1962-1973 (2017)
AbstractA 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.
Identifiersdoi: 10.1021/acs.organomet.7b00102
e-issn: 1520-6041
issn: 0276-7333
Appears in Collections:(ISQCH) Artículos
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