131423-29-5Relevant articles and documents
Palladium-catalyzed cross-coupling reactions of triarylbismuthanes with terminal alkynes under aerobic conditions
Matsumura, Mio,Yamada, Mizuki,Tsuji, Toshiyuki,Murata, Yuki,Kakusawa, Naoki,Yasuike, Shuji
, p. 70 - 75 (2015)
Abstract A simple Pd-catalyzed Sonogashira-type cross-coupling reaction using of triarylbismuthanes is described. The reaction of triarylbismuthanes with terminal alkynes in the presence of 5 mol% of Pd(OAc)2, 6 equiv. AgF and 6 equiv. K3PO4 at room temperature afforded the coupling products in good to excellent yield. The reaction proceeded effectively under aerobic conditions, and all three aryl groups on bismuth could be transferred to the coupling products. The reaction was sensitive to the electronic nature of the triarylbismuthanes: substrates bearing an electron-withdrawing group on the aromatic ring showed higher reactivity than those having an electron-donating group.
Carboxylate-based, room-temperature ionic liquids as efficient media for palladium-catalyzed homocoupling and sonogashira-hagihara reactions of aryl halides
Iranpoor, Nasser,Firouzabadi, Habib,Ahmadi, Yasaman
, p. 305 - 311 (2012)
Carboxylate-based salts are introduced as easily prepared, cheap and stable ionic liquids (ILs) that act as the base, ligand, reducing agent and media for the efficient phosphane-free, palladium-catalyzed homocoupling reaction of aryl iodides and bromides. The efficient copper and phosphane-free Sonagashira coupling reaction of aryl iodides and bromides is also demonstrated in these ILs. One of the ILs was also phosphorylated and showed high efficiency and recyclability as a medium, and was also used as a ligand for palladium-catalyzed homocoupling and copper-free Sonogashira reactions of aryl iodides and bromides. Copyright
Transition-Metal-Free Sonogashira-Type Coupling Reactions in Water
Appukkuttan, Prasad,Dehaen, Wim,Van Der Eycken, Erik
, p. 4713 - 4716 (2003)
Microwave-assisted transition-metal-free Sonogashira-type coupling reactions are described. The reactions are run in water as the sole solvent, without the need for copper(I) or any transition-metal-phosphane complex. The scope of the methodology was tested by reaction of a wide variety of aryl halides and heteroaryl halides. The reaction was also investigated under conventional heating conditions. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
An efficient ligand- and copper-free Sonogashira reaction catalyzed by palladium nanoparticles supported on pectin
Khazaei, Ardeshir,Rahmati, Sadegh,Saednia, Shahnaz
, p. 9 - 13 (2013)
A novel and green procedure for synthesis of Palladium nanoparticles (2-6 nm) supported on pectin, as a reductant and ligand is described. The synthesized catalyst was further successfully explored in copper, ligand-and amine-free Sonogashira-Hagihara cou
Efficient and General Protocol for the Copper-Free Sonogashira Coupling of Aryl Bromides at Room Temperature
Soheili, Arash,Albaneze-Walker, Jennifer,Murry, Jerry A.,Dormer, Peter G.,Hughes, David L.
, p. 4191 - 4194 (2003)
(Equation presented) A mild and general protocol for the copper-free Sonogashira coupling of aryl bromides with acetylenes has been developed. The use of (AllylPdCl)2 and P(t-Bu)3 provides the active Pd(0) catalyst that allows subseq
Dendrimer-encapsulated Pd(0) nanoparticles immobilized on nanosilica as a highly active and recyclable catalyst for the copper- and phosphine-free Sonogashira-Hagihara coupling reactions in water
Esmaeilpour, Mohsen,Sardarian, Alireza,Javidi, Jaber
, p. 4005 - 4019 (2016)
This study demonstrates a new synthetic strategy for the preparation of porous SiO2 for catalytic applications using natural and waste materials from rice husks as the source of biosilica. Biogenic porous silica nanoparticles with a mean diameter of 45 nm were successfully prepared from rice husk (RH) biomass via a new multistep method. During the first step, sodium silicate is extracted from rice husks. Then, cetyltrimethylammonium bromide (CTAB), HCl, and HOAc were added into sodium silicate solution, and the resulting mixture was sonicated. After the hydrothermal reaction, the collected samples were calcinated to obtain silica nanoparticles. Then, dendrimer-encapsulated Pd(0) nanoparticles supported on nano-silica with surface amino groups were fabricated. These materials are prepared by sequestering palladium ions within dendrimers followed by chemical reduction to yield the corresponding zero-valent palladium nanoparticles. The synthesized nanostructures were characterized by X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), Fourier transform infrared (FT-IR) spectroscopy, thermogravimetric analysis (TGA), dynamic light scattering (DLS), N2 adsorption-desorption isotherm analysis, UV-vis spectroscopy and elemental analysis. The morphologies of the catalyst were characterized using a field emission scanning electron microscope (FE-SEM) and a transmission electron microscope (TEM). Also, its Pd content was determined by using an inductively coupled plasma (ICP) analyzer. This catalytic system was used as an efficient catalyst for Sonogashira reaction of aryl halides with alkynes under copper and phosphine ligand-free conditions in water. The catalyst was regenerated for five cycles of reaction without any significant loss in its activity. Also, the analysis of the reaction mixture by the ICP technique showed that the leaching of the catalyst was negligible.
Decarbonylative Sonogashira Cross-Coupling of Carboxylic Acids
Liu, Chengwei,Szostak, Michal
supporting information, p. 4726 - 4730 (2021/06/28)
Decarbonylative Sonogashira cross-coupling of carboxylic acids by palladium catalysis is presented. The carboxylic acid is activated in situ by the formation of a mixed anhydride and further decarbonylates using the Pd(OAc)2/Xantphos system to provide an aryl-Pd intermediate, which is intercepted by alkynes to access the traditional Pd(0)/(II) cycle using carboxylic acids as ubiquitous and orthogonal electrophilic cross-coupling partners. The methodology efficiently constructs new C(sp2)-C(sp) bonds and can be applied to the derivatization of pharmaceuticals. Mechanistic studies give support to decarbonylation preceding transmetalation in this process.
Shuttling Catalyst: Facilitating C?C Bond Formation via Cross-Couplings with a Thermoresponsive Polymeric Ligand
Wang, Erfei,Zhang, Jiawei,Zhong, Zhuoran,Chen, Kaixuan,Chen, Mao
, p. 419 - 423 (2020/01/08)
A poly(ethylene glycol) (PEG) linked ortho-MeO-phenyldicyclohexylphosphine (MeO-WePhos) ligand has been synthesized to promote Pd-catalyzed carbon-carbon bond formation by cross-couplings including Sonogashira, Heck, Hiyama and Stille reactions, providing corresponding (hetero)aryl substituted alkynes, alkenes and bi(hetero)aryls in good to excellent isolated yields with low Pd loadings. Facilitated by the lower critical solution temperature behaviour of the polymeric monophosphine ligand, the metal-complex could rapidly shuttle between organic and water phases as regulated by temperature, enabling highly efficient catalyst recycling via a simple phase separation. The chemical structure of ligand was determined by matrix-assisted laser desorption/ionization-time of flight mass spectrometry, nuclear magnetic resonance spectrometry and size-exclusion chromatography measurements. Notably, as demonstrated by the inductively coupled plasma-atomic emission spectrometry measurement, 98% Pd was kept in the water phase after 6 cycles of catalyst recycling experiments. Given the profound impact of transition-metal-catalyzed covalent bond formation and the increasing demand of sustainable chemistry, this work provides an alternative method to conduct cross-couplings with a polymeric shuttling catalyst.
