29822-79-5Relevant articles and documents
Yoshida,Fueno
, p. 711 (1970)
Palladium nanoclusters in Sonogashira cross-coupling: A true catalytic species?
Thathagar, Mehul B.,Kooyman, Patricia J.,Boerleider, Romilda,Jansen, Eveline,Elsevier, Cornelis J.,Rothenberg, Gadi
, p. 1965 - 1968 (2005)
The question of whether palladium nanoclusters are the actual catalysts in the so-called 'cluster-catalyzed Sonogashira cross-coupling' is investigated, using the coupling of phenylacetylene with 4-bromobenzonitrile as a model reaction. By combining a detailed kinetic analysis with transmission electron microscopy (TEM), we show that a soluble species must be present in the system when Pd nanoclusters are used as catalysts. Various Pd clusters show similar kinetic profiles to that of a homogeneous Pd(dba)2 complex. Most importantly, TEM analysis of samples taken before, during, and after the reaction shows that the cluster size decreases during the reaction. Based on these findings, we present a possible two-path mechanism for Sonogashira cross-coupling reactions in the presence of Pd nanoclusters.
Xantphos-coordinated palladium dithiolates: Highly efficient catalyst for decarboxylative Sonogashira reaction into corresponding alkynes
Lokolkar, Manjunath S.,Mane, Pravin A.,Dey, Sandip,Bhanage, Bhalchandra M.
, (2021/06/25)
This work reports Xantphos-coordinated palladium dithiolate complexes as catalysts for decarboxylative Sonogashira coupling reaction of phenyl propiolic acid and 2-butynoic acid with various iodoarenes. These palladium aryl dithiolate complexes were synthesized and characterized by 1H and 31P nuclear magnetic resonance (NMR) spectroscopy, melting point, and elemental analysis (CHNS). Synthetic utility for the reported protocol is explored for the effect of various functional groups on the yield of corresponding heteroaryl alkynes. The current protocol showed excellent catalytic activity towards decarboxylative alkynylation reaction with high turn-over number (TON) up to 105 and turn-over frequency (TOF) up to 104 h?1. The catalyst could be recycled up to six recycles without losing its catalytic activity. The in situ generation of palladium nanoparticles (PdNPs) was observed after the third recycle, and the amount was significant after the sixth recycle, which were confirmed and characterized by powder X-ray diffraction (XRD), scanning electron microscope (SEM), and energy-dispersive X-ray (EDX) analysis and high-resolution transmission electron microscopy (HR-TEM). The catalytic activity of the reaction is attributed to the formation of PdNPs.
Co3O4 nanoparticles embedded in triple-shelled graphitic carbon nitride (Co3O4/TSCN): a new sustainable and high-performance hierarchical catalyst for the Pd/Cu-free Sonogashira–Hagihara cross-coupling reaction
Ghodsinia, Sara S. E.,Akhlaghinia, Batool,Jahanshahi, Roya
, p. 3217 - 3244 (2021/05/17)
Inspired by the synthesis of triple-shelled periodic mesoporous organosilica hollow spheres, a straightforward and controllable approach for the preparation of Co3O4 NPs embedded in triple-shelled graphitic carbon nitride has been es