Modified palladium-catalyzed Sonogashira cross-coupling reactions under copper-, amine-, and solvent-free conditions

Liang, Yun,Xie, Ye-Xiang,Li, Jin-Heng

, p. 379 - 381 (2006)

PdCl2(PPh3)2 combined with TBAF under solvent-free conditions provided general and fast Sonogashira cross-coupling reactions of aryl halides with terminal alkynes. In particular, this protocol could be applied to the reactions of deactivated aryl chlorides. In the presence of 3 mol % of PdCl2(PPh3)2 and 3 equiv of TBAF, a number of ArX species (X = I, Br, Cl) were coupled with alkynes to afford the corresponding products in moderate to excellent yields under copper-, amine-, and solvent-free conditions.

Palladium nanoparticles supported on modified polystyrene resin as a polymeric catalyst for Sonogashira-Hagihara coupling reactions

Tamami, Bahman,Nowroozi Dodeji, Fatemeh,Ghasemi, Soheila

, p. 880 - 885 (2015)

Pd(0) nanoparticles supported on modified crosslinked polystyrene were synthesized and characterized. Crosslinked polystyrene was reacted with trioxane and chlorotrimethylsilane in the presence of SnCl4 to form Merrifield resin. The Merrifield

Sioda et al.

, p. 230 (1967)

A versatile catalyst for the sonogashira coupling of aryl chlorides

Koellhofer, Axel,Pullmann, Thomas,Plenio, Herbert

, p. 1056 - 1058 (2003)

Aryl chlorides are suitable substrates for the Sonogashira coupling! By using the versatile catalyst system Na2[PdCl4]/PR3/ Cul (PR3= (1-Ad)2PBn, PtBu3), the Sonogashira coupling [Eq. (a)] of aryl chlorides with alkynes generates excellent yields of the corresponding disubstituted aryl alkynes.

Copper(II) acetate/1,4-diphenyl-1,4-diazabuta-1,3-diene catalyzed sonogashira cross-coupling of aryl halides with terminal alkynes under aerobic and solvent-free conditions

Deng, Chen-Liang,Xie, Ye-Xiang,Yin, Du-Lin,Li, Jin-Heng

, p. 3370 - 3376 (2006)

The Sonogashira cross-coupling of aryl halides with terminal alkynes catalyzed by an inexpensive copper(II) acetate/1,4-diphenyl-1,4-diazabuta-1,3- diene [Cu(OAc)2/DAB-Ph] catalytic system is reported. A series of ligands, including diazabutadiene systems, N,N-dimethylglycine, L-proline, ethylenediamine, and phosphines, were evaluated, and 1,4-diphenyl-1,4-diazabuta- 1,3-diene provided the best results. In the presence of copper(II) acetate (10 mol%), 1,4-diphenyl-1,4-diazabuta-1,3-diene (20 mol%), and tetrabutylammonium fluoride (3 equiv), a number of aryl iodides or bromides were treated smoothly with alkynes to afford the corresponding products in moderate to excellent yields. It is noteworthy that the reaction is conducted under aerobic and solvent-free conditions. Georg Thieme Verlag Stuttgart.

Phosphine-free Sonogashira coupling: reactions of aryl halides catalysed by palladium(II) complexes of azetidine-derived polyamines under mild conditions

Lee, Dong-Hwan,Lee, Young Hoon,Harrowfield, Jack M.,Lee, Ik-Mo,Lee, Hong In,Lim, Woo Taik,Kim, Yang,Jin, Myung-Jong

, p. 1630 - 1634 (2009)

Readily synthesised, water-stable pyridylazetidine-based Pd(II) complexes have been studied as catalysts for the Sonogashira coupling reaction. Under low catalyst loadings, various aryl bromides and chlorides were efficiently coupled with phenylacetylene

Copper(I)-catalyzed Caryl-Calkynyl bond formation of aryl iodides with terminal alkynes

Thakur,Sekar

, p. 2785 - 2789 (2009)

A wide range of internal alkynes are synthesized from the corresponding aryl iodides and terminal alkynes by Sonogashira-type cross-coupling reactions through Caryl-Calkynyl bond formation in the presence of a catalytic amount of readily available DBU-CuBr complex under mild reaction conditions. Georg Thieme Verlag Stuttgart.

Recycling of homogeneous Pd catalysts using superparamagnetic nanoparticles as novel soluble supports for Suzuki, Heck, and Sonogashira cross-coupling reactions

Stevens, Philip D.,Li, Guifeng,Fan, Jinda,Yen, Max,Gao, Yong

, p. 4435 - 4437 (2005)

Recycling of homogeneous catalysts could be achieved by using magnetic nanoparticles and solid-phase beads, but nanoparticle-supported catalysis proceeded much faster than its counter-part on resins. The Royal Society of Chemistry 2005.

The effect of steric bulk in Sonogashira coupling reactions

An Der Heiden, Markus,Plenio, Herbert

, p. 972 - 974 (2007)

The rates of Sonogashira coupling reactions using [Pd-PR3] complexes depend on a combination of the steric bulk of phosphines and substrates; however, below a critical cone angle of ca. 170° the catalytic activity drops drastically. The Royal S

Zeolite-based copper catalyst for decarboxylative coupling of alkynyl carboxylic acids with aryl iodides

Park, Jaerim,Jung, Dasom,Kim, Han-Sung,Na, Kyungsu,Lee, Sunwoo

, p. 83 - 88 (2017)

A series of nanoporous aluminosilicate materials (zeolite FAU(Y), LTA(A), and mesoporous Al-SBA-15) was prepared to investigate their catalytic performances in decarboxylative coupling reactions of alkynyl carboxylic acids with aryl iodides. The aluminosilicate frameworks were used for binding Cu(II) ions without coordination by organic ligands. Effects of pore size and Cu(II) content of the aluminosilicates on the catalytic activity and product yield were investigated by varying the solvent, base, and functional groups in the reactants. This catalytic system provided high yields and good selectivity for the desired diaryl alkynes. In addition, the Cu(II)-exchanged zeolite Y catalyst which is NaCuY(0.11) exhibited high recyclability, showing no significant change in catalytic performance after six repetitions.

Step-by-step synthesis of copper(I) complex supported on platinum nanoparticle-decorated mesoporous silica hollow spheres and its remarkable catalytic performance in Sonogashira coupling reaction

Abolhosseini Shahrnoy, Abdolghafar,Mahjoub, Ali Reza,Shokrollahi, Sudabeh,Ezzati, Nasim,Elsner, Kristiane,Koch, Christoph T.

, (2020)

In this study, a step-by-step method for the synthesis of platinum nanoparticles and copper(I) complex supported on mesoporous silica hollow spheres (Pt-MSHSs-Cu) is introduced. Scanning electron microscopy, transmission electron microscopy, powder X-ray

Visible-light-enhanced photocatalytic Sonogashira reaction over silicon carbide supported Pd nanoparticles

Wang, Bing,Guo, Xiaoning,Jin, Guoqiang,Guo, Xiangyun

, p. 81 - 84 (2017)

Sonogashira reaction of aryl halides with terminal alkynes can be realized by a visible-light-driven heterogeneous catalytic route using silicon carbide supported Pd nanoparticles as the catalyst under copper-, and ligand-free conditions. Under the irradi

Efficient and copper-free Pd(OAc)2/DABCO-catalyzed Sonogashira cross-coupling reaction

Li, Jin-Heng,Zhang, Xu-Dong,Xie, Ye-Xiang

, p. 804 - 808 (2005)

An efficient and copper-free palladium-catalyzed Sonogashira cross-coupling reaction protocol is presented. In the presence of 3 mol% of Pd(OAc) 2 and 6 mol% of DABCO, cross-coupling of various aryl halides (iodides and bromides) with terminal

Immobilized palladium nanoparticles on silica functionalized N-propylpiperazine sodium N-propionate (SBPPSP): Catalytic activity evaluation in copper-free Sonogashira reaction

Niknam, Khodabakhsh,Deris, Abdollah,Panahi, Farhad,Reza Hormozi Nezhad

, p. 1291 - 1296 (2013)

An efficient heterogeneous palladium catalyst system has been developed based on immobilization of Pd nanoparticles on silica-bonded N-propylpiperazine sodium N-propionate (SBPPSP) substrate. SBPPSP substrate can stabilize the Pd nanoparticles effectively

Synthesis and characterization of Schiff base complex of Pd(II) supported on superparamagnetic Fe3O4@SiO2 nanoparticles and its application as an efficient copper- and phosphine ligand-free recyclable catalyst for Sonogash

Esmaeilpour, Mohsen,Sardarian, Ali Reza,Javidi, Jaber

, p. 233 - 240 (2014)

Superparamagnetic nanoparticles functionalized with Schiff base complex of Pd (II) were simply synthesized by a two-step method. The catalyst was characterized by X-ray powder diffraction (XRD), field emission scanning electron microscopy (FE-SEM), transm

Alkynyl germatranes as alternative reagents for the preparation of biarylethynes

Faller, Jack W.,Kultyshev, Roman G.,Parr, Jonathan

, p. 451 - 453 (2003)

Arylalkynyl germatranes react with aryl chlorides and triflates to give the corresponding biarylethynes in good yield. The reaction proceeds under mild conditions in the presence of a palladium phosphine catalyst and fluoride ions.

Functionalization of multi-walled carbon nanotubes with pramipexole for immobilization of palladium nanoparticles and investigation of catalytic activity in the Sonogashira coupling reaction

Abbasi, Sahar,Hekmati, Malak

, (2017)

Pramipexole drug was attached to the surface of multi-walled carbon nanotubes (MWCNTs) by reaction of acylated carbon nanotubes with pramipexole for the first time. The modified MWCNTs were characterized using Fourier transform infrared spectroscopy, tran

Sonogashira cross-coupling reactions of aryl chlorides with alkynes catalysed by a tetraphosphine-palladium catalyst

Feuerstein, Marie,Doucet, Henri,Santelli, Maurice

, p. 8443 - 8446 (2004)

A range of aryl chlorides undergoes cross-couplings with alkynes in good yields in the presence of [PdCl(C3H5)]2/cis, cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane as catalyst. A variety of aryl chlorides such as chloroacetophenone, chlorobenzonitrile, chloronitrobenzene, chloroanisole or chlorotoluene have been used successfully. The reaction also tolerates several alkynes such as phenylacetylene, dec-1-yne, ethynylcyclohexene or alk-1-ynols. Furthermore, this catalyst can be used at low loading with some substrates.

Chelidamic acid functionalized stimuli-responsive hydrogel supported-palladium catalyst for copper-free Sonogashira reaction in aqueous media

Yang, Jianhua,Zhang, Xi,Yu, Wei,Liu, Weijie,Bian, Fengling

, p. 710 - 718 (2013)

A thermo and pH-responsive hydrogel (PNIPAM-co-PPAP) was synthesized via free radical polymerization of N-isopropylacrylamide (NIPAM) and potassium 4-(acryloyloxy) pyridine-2, 6-dicarboxylate (PAP) in mixed solvents of water and tetrahydrofuran. SEM micro

A series of (NHC)Pd(N?O)(OAc) complexes: synthesis, characterization and catalytic activities towards desulfinative Sonogashira coupling of arylsulfonyl hydrazides with arylalkynes

Lu, Jian-Zhong,Wang, Tian,Yang, Jin,Zhao, Ya-Yu,Zhu, Guang-Hao

, (2020)

A series of well-defined N-heterocyclic carbene palladium (II) complexes with general formula (NHC)Pd(N?O)(OAc) were prepared through reaction of Pd (NHC)(OAc)2(H2O) with 1-methyl-1H-pyrazole-3-carboxylic acid or 1-methyl-1H-indazole-3-carboxylic acid in the presence of K2CO3. These complexes were then used for desulfinative Sonogashira coupling of arylsulfonyl hydrazides with terminal alkynes. With low catalyst loading, all synthesized palladium compounds exhibited moderate to high catalytic activities for the reactions.

Simple and efficient diaryl alkyne synthesis method

-

Paragraph 0026; 0029-0031, (2021/04/14)

The embodiment of the invention discloses a simple and efficient diaryl alkyne synthesis method. The method comprises the steps of by taking arylmethylbenzotriazole and aromatic aldehyde as raw materials, carrying out addition and double-beta-elimination reaction under the action of bis (trimethylsilyl) amino salt MN (SiMe3) 2 to synthesize diaryl alkyne by a one-pot method. The raw materials and chemical reagents used in the method are easy to obtain, the reaction conditions are mild, the operation is simple, the substrate universality is good, the product yield is high, and the method is a simple and efficient diaryl alkyne synthesis method.

A Waste-Minimized Approach to Cassar-Heck Reaction Based on POLITAG-Pd0 Heterogeneous Catalyst and Recoverable Acetonitrile Azeotrope

Valentini, Federica,Ferlin, Francesco,Tomarelli, Elena,Mahmoudi, Hamed,Bagherzadeh, Mojtaba,Calamante, Massimo,Vaccaro, Luigi

, p. 3359 - 3366 (2021/07/28)

Three different Pd0-based heterogeneous catalysts were developed and tested in the Cassar–Heck reaction (i. e., copper-free Sonogashira reaction) aiming at the definition of a waste minimized protocol. The cross-linked polymeric supports used in this investigation were designed to be adequate for different reaction media and were decorated with different pincer-type ionic ligands having the role of stabilizing the formation and dimension of palladium nanoparticles. Among the ionic tags tested, bis-imidazolium showed the best performances in terms of efficiency and durability of the metal catalytic system. Eventually, aqueous acetonitrile azeotrope was selected as the reaction medium as it allowed the best catalytic efficiency combined with easy recovery and reuse. Finally, the synergy between the selected catalyst and reaction medium allowed to obtain highly satisfactory isolated yields of a variety of substrates while using a low amount of metal catalyst. The high performance of the designed POLymeric Ionic TAG (POLITAG)-Pd0, along with its good selectivity achieved in a copper-free process, also led to a simplified purification procedure allowing the minimization of the waste generated as also proven by the very low E-factor values (1.4–5) associated.