Ligand Free Heterogeneous Sonogashira Cross-Coupling Reaction over an in Situ Organoiodine Capsulized Palladium Anchored to a Perovskite Catalyst

Abstract

An environmentally friendly Sonogashira cross-coupling reaction is described in this study with high potential for application in a fluidized system. The LaCo0.9Ni0.05Pd0.05O3 perovskite based catalyst provided a high turnover frequency (TOF) of 900 h–1 via mainly a heterogeneous mechanism in an environmentally friendly mixed medium of water and acetonitrile. Nanosized Pd(0) sites were anchored to the surface of perovskite using an in situ formed colloidal agent. This capsulizing agent was found to consist of organic compounds containing iodine atoms that interacted strongly with basic sites of the hydrophobic perovskite carrier using adsorption forces. This study illustrates a unique and strong principle for designing green heterogeneous catalysts for common valuable organic reactions.

Pd Nanoparticles-Loaded Honeycomb-Structured Bio-nanocellulose as a Heterogeneous Catalyst for Heteroaryl Cross-Coupling Reaction

“…Similarly, the reported catalysts for the Sonogashira cross-coupling reaction Pd-MNPSS and Pd/perovskite require relatively high reaction temperatures and their preparation methods are neither economical nor sustainable compared to PdNPs@NCmw. The requirement of a special setup and copper cocatalysts for Pd/TNS and cell–OOCPhPPh 2 –Pd, respectively, are significant drawbacks for these two heterogeneous catalysts.…”

Recent Expedition inPd‐CatalyzedSonogashira Coupling and Related Processes†

“…[ 101 ] Meanwhile, Friedrich disclosed a LaCo 0.9 Ni 0.05 Pd 0.05 O 3 perovskite based catalyst system that the nanosized Pd(0) sites were anchored to the surface of perovskite using an in situ formed colloidal agent. [ 102 ] The Sonogashira coupling proceeded smoothly using 1.0 mol% Pd with high TOFs of 900 h –1 .…”

Self‐assembly aryl cyclopalladated imine film supported on the silicon surface—Fabrication, formation of active PdPd/PdO sites, and catalytic properties for Sonogashira cross‐coupling reaction

“…Among many supports, [23][24][25][26] silicon wafers have drawn growing interest due to their regular surface and chemical stability, providing the active site on the regular surface and the ordered chemical organometallic films as an investigating platform. [27][28][29][30][31][32][33][34][35][36][37][38][39][40][41][42][43][44][45] Self-assembly method (SAM) provides a customized design, controllable arrangement, easy reproduce and stable monolayer, and the surface structure of the catalyst film on the supports is also an important factor affecting the activity, 46 which can be endowed through modifying the surface of catalyst by using SAM. The regular surface can be used as an ideal platform to elucidating the catalytic mechanism, [47][48][49][50][51][52] on which the structure, the real active center and the change of active sites can be easily detected and elucidated.…”

“…How to design the heterogeneous catalyst easily obtained with high activity is one of the most challenges. Among many supports, 23–26 silicon wafers have drawn growing interest due to their regular surface and chemical stability, providing the active site on the regular surface and the ordered chemical organometallic films as an investigating platform 27–45 …”