1144-74-7Relevant articles and documents
Carbonylative cross-coupling reaction of ethynylstibane with aryl iodides
Kakusawa, Naoki,Kurita, Jyoji
, p. 699 - 702 (2006)
Palladium-catalyzed carbonylative cross-coupling reaction of ethynylstibane (Ph-=-SbPh2) and aryl iodides (Ar-I) is described. The reaction of the stibanes and the halides under 1 atm of carbon monoxide in N,N-dimethylacetamide using a combination of 5 mol% Pd(OAc)2 and 4 equivalents (20 mol%) of PPh3 brought about carbonylative cross-coupling reaction to afford arylethynylketones [ArC(O)-=-Ph] in good yields along with a small amount of directly coupled products, aryl acetylens (Ar-=-Ph). Formation of the side product was completely suppressed by conducting the reaction under high CO pressure (20 atm) conditions. The present method provides a variety of carbonylated products in good yield even with electron-deficient aryl iodides which usually give inferior results due to their tendency to undergo decarbonylation in the cross-coupling reaction of ethynylstibanes and acyl halides.
Highly efficient etherification and oxidation of aromatic alcohols using supported and unsupported phosphorus pentoxide as a heterogeneous reagent
Khazaei, Ardeshir,Rad, Mohammad Navid Soltani,Borazjani, Maryam Kiani,Saednia, Shahnaz,Borazjani, Mohammad Kiani,Golbaghi, Maryam,Behrouz, Somayeh
, p. 1544 - 1553 (2011)
A highly efficient procedure for etherification and oxidation of aromatic alcohol is described using unsupported and supported P2O5 on alumina and/or silica gel. The silica gel and alumina proved to be the most suitable support among the supports examined in our experiments. It was illustrated that the etherification and oxidative performance in reactions depend largely upon variables including reaction temperature, the nature of the P2O5 used (supported or unsupported P2O 5), and whether solvent-free conditions are applied. It was shown that P2O5 not only can convert the aromatic alcohols into corresponding ethers and/or aldehyde and ketone but also can convert aromatic ethers into aldehyde or ketone via oxidative cleavage. Finally, quantum mechanical calculations were performed to rationalized these events, and it was indicated that aldehyde and ketone are more favorable products on the basis of the heat of formation (Hf).
Room-temperature palladium-catalyzed and copper(I)-mediated coupling reactions of acid chlorides with boronic acids under neutral conditions
Nishihara, Yasushi,Inoue, Yoshiaki,Fujisawa, Mamoru,Takagi, Kentaro
, p. 2309 - 2312 (2005)
The palladium-catalyzed cross-coupling reactions of acid chlorides with arylboronic acids in the presence of copper(I) thiophene-2-carboxylate (CuTC) as an activator under strictly non-basic and mild reaction conditions afford the unsymmetrical ketones in moderate to excellent yields. A wide range of substrates bearing an electron-donating or an electron-withdrawing substituent on the aromatic ring is compatible. Georg Thieme Verlag Stuttgart.
Silica-supported phosphine palladium(0) complex catalyzed phenylation of acid chlorides and aryl iodides by sodium tetraphenylborate
Cai, Ming-Zhong,Song, Cai-Sheng,Huang, Xian
, p. 693 - 700 (1998)
In the presence of a catalytic amount of silica - supported phosphine palladium(0) complex, sodium tetraphenylborate (NaBPh4) reacts with acid chlorides under mild conditions to give the corresponding phenyl ketones in 57-80% yields; it also reacts with aryl iodides to afford the corresponding biaryls in 75-84% yields.
Palladium-catalyzed direct conversion of carboxylic acids into ketones with organoboronic acids promoted by anhydride activators
Yamamoto,Kakino,Narahashi,Shimizu
, p. 1333 - 1345 (2002)
A new type of catalytic process to convert carboxylic acids and organoboron compounds into unsymmetrical ketones in one-pot under mild and neutral conditions was presented. The method allowed the use of an α, β-unsatuarted carboxylic acids such as trans-c
Successful application of indirect electrooxidation for the transformation of biaryl methanols to the corresponding biaryl ketones
Okimoto, Mitsuhiro,Yoshida, Takashi,Hoshi, Masayuki,Chiba, Tomohito,Maeo, Kei
, p. 3134 - 3139 (2011)
Various biaryl methanols were electrooxidized into the corresponding biaryl ketones in good yields and under very mild reaction conditions. Because of the relatively high oxidation potential, bulky structure, and somewhat poor solubility, biaryl methanols do not readily undergo direct electrooxidative transformations as a synthetic step toward the corresponding biaryl ketones. Herein, we report the successful indirect electrooxidation of secondary biaryl methanols featuring the use of a slight excess amount of KI (1.2 equivalents, relative to the substrate) in MeOH. Copyright
Reaction of pentaarylantimony with acid halide, aldehyde and ketone
Fujiwara, Masahiro,Tanaka, Mutsuo,Baba, Akio,Ando, Hisanori,Souma, Yoshie
, p. 49 - 52 (1996)
Pentaarylantimony (pentaphenylantimony, penta-p-tolylantimony and penta-p-chlorophenylantimony) was found to be a mild arylation reagent. The arylation was chemoselective toward aromatic acid halides to give the corresponding aromatic ketones. No direct addition to ketone and acid anhydride occurred. Arylation reactions of aldehyde or ketone were promoted by the addition of Lewis acid. The nucleophilicities of aromatic antimony compounds depend on the number of antimony-aromatic carbon bonds.
Pd/C: An efficient, heterogeneous and reusable catalyst for phosphane-free carbonylative suzuki coupling reactions of aryl and heteroaryl iodides
Khedkar, Mayur V.,Tambade, Pawan J.,Qureshi, Ziyauddin S.,Bhanage, Bhalchandra M.
, p. 6981 - 6986 (2010)
The carbonylative Suzuki coupling reaction of aryl boronic acid with different aryl and heteroaryl iodides was carried out to synthesize various unsymmetrical biaryl ketones by using Pd/C as an efficient, heterogeneous and reusable catalyst. The catalyst exhibits remarkable activity, and its reusability was tested up to four consecutive cycles. The reaction is applicable for various aryl and heteroaryl iodides having different steric and electronic properties. It provides good to excellent yield of the desired products. The developed protocol is advantageous with regard to the ease in handling the catalyst and the simple work-up procedure; it is also an environmentally benign process with effective catalyst recyclability. A facile protocol has been developed for the carbonylative Suzuki coupling reaction of aryl and heteroaryl iodides with Pd/C as effective, heterogeneous, reusable catalyst. The system is applicable for a wide variety of aryl and heteroaryl iodides. Copyright
Palladium-catalyzed carbonylative cross-coupling reaction of triarylantimony dicarboxylates with arylboronic acids: Synthesis of biaryl ketones
Qin, Weiwei,Yasuike, Shuji,Kakusawa, Naoki,Kurita, Jyoji
, p. 2949 - 2953 (2008)
A novel palladium-catalyzed three-component carbonylative coupling reaction by use of triarylantimony diacetate, arylboronic acid and carbon monoxide (1 atm) could be attained under mild reaction conditions without any base as an additive. The reaction can be applied to a wide range of triarylantimony diacetates and boronic acids to afford the corresponding unsymmetrical biaryl ketones in good yields.
Rhodium-catalyzed synthesis of aryl ketones from carboxylic acid anhydrides and potassium aryltrifluoroborates in the presence of CuI
Liu, Xia,Yi, Ze,Yi, Maocong,Wang, Jianhui,Liu, Guiyan
, p. 4635 - 4639 (2015)
A new rhodium-catalyzed cross-coupling of carboxylic acid anhydrides and potassium aryltrifluoroborates was described. In this system CuI played a very important role. Various functionalities were compatible in the reaction, and the desired products were obtained in good to excellent yields. A mechanism of this reaction using a Rh(I) model catalyst have also been proposed.
Iron-catalyzed carbonylation of aryl halides with arylborons using stoichiometric chloroform as the carbon monoxide source
Zhao, Hongyuan,Du, Hongyan,Yuan, Xiaorong,Wang, Tianjiao,Han, Wei
, p. 5782 - 5787 (2016)
A general iron-catalyzed carbonylative Suzuki-Miyaura coupling of aryl halides with arylborons is reported, using stoichiometric CHCl3 as the CO source. The high efficiency, economy, selectivity, and operational simplicity of this transformation make this method a valuable tool in organic synthesis. Importantly, the presented strategy allows effective 13C labeling simply by using the commercially available 13C-labeled CHCl3. On the basis of the initial mechanistic exploration, an aryl radical intermediate is proposed in the present carbonylation process.
Efficient N-heterocyclic carbene palladium(II) catalysts for carbonylative Suzuki-Miyaura coupling reactions leading to aryl ketones and diketones
Ibrahim, Mansur,Malik, Imran,Mansour, Waseem,Sharif, Muhammad,Fettouhi, Mohammed,El Ali, Bassam
, p. 44 - 51 (2018)
New N, N′-substituted imidazolium salts (L1 and L2) and their corresponding diiodopyridinepalladium(II) complexes (C1 and C2) were successfully synthesized and characterized. Reactions of palladium iodide with the newly synthesized N, N′-substituted imidazolium iodides in pyridine afforded the corresponding new palladium-N-heterocyclic carbene pyridine complexes in high yields. The new palladium(II) complex C1 was characterized by single crystal X-ray diffraction analysis. The Pd(II) ion is bonded to the nitrogen atom of the pyridine, the carbon atom of the NHC carbene ligand and two trans iodides resulting in distorted square planar geometry. The two Pd-NHC-Py complexes C1 and C2 displayed higher catalytic activity in the carbonylative Suzuki-Miyaura coupling reactions with much lower catalyst loading as compared to the catalytic systems reported in the literature.
Cu (II) Schiff base complex grafted guar gum: Catalyst for benzophenone derivatives synthesis
Krishna,Kumari, Shweta,Sharma, Sunil K.,Yadav, Deepak
, (2020)
In this study Guar gum based Cu(II) Schiff's base complex (GG-Cu) has been synthesized and characterized by FT-IR, PXRD, UV–vis, TGA, XPS, FESEM, TEM, EDAX, solid-state NMR, Elemental mapping, CHNS and AAS analysis. This moiety has been found to be an efficient heterogeneous catalyst for selective oxidation reactions. Fifteen model reactions have been carried to establish the catalytic behavior of GG-Cu, and five of these yield novel products. The ease of separation of catalyst from the reaction mixture simply by filtration is an added advantage; furthermore the catalyst can be reused up to five times without significant loss of catalytic activity. The overall concept of developing newer, efficient and environmental benign catalysts with ease of separation and recycling ability has been successfully demonstrated. All of the isolated products were fully characterized on the basis of their physical and spectral data.
Novel palladium nanoparticles supported on β-cyclodextrin@graphene oxide as magnetically recyclable catalyst for Suzuki–Miyaura cross-coupling reaction with two different approaches in bio-based solvents
Heidari, Bahareh,Heravi, Majid M.,Nabid, Mohammad Reza,Sedghi, Roya,Hooshmand, Seyyed Emad
, (2019)
A novel nanocatalyst was designed and prepared. Initially, the surface of magnetic graphene oxide (M-GO) was modified using thionyl chloride, tris(hydroxymethyl)aminomethane and acryloyl chloride as linkers which provide reactive C═C bonds for the polymerization of vinylic monomers. Separately, β-cyclodextrin (β-CD) was treated with acryloyl chloride to provide a modified β-CD. Then, in the presence methylenebisacrylamide as a cross-linker, monomers of modified β-CD and acrylamide were polymerized on the surface of the pre-prepared M-GO. Finally, palladium acetate and sodium borohydride were added to this composite to afford supported palladium nanoparticles. This fabricated nanocomposite was fully characterized using various techniques. The efficiency of this easily separable and reusable heterogeneous catalyst was successfully examined in Suzuki–Miyaura cross-coupling reactions of aryl halides and boronic acid as well as in modified Suzuki–Miyaura cross-coupling reactions of N-acylsuccinimides and boronic acid in green media. The results showed that the nanocatalyst was efficient in coupling reactions for direct formation of the corresponding biphenyl as well as benzophenone derivatives in green media based on bio-based solvents. In addition, the nanocatalyst was easily separable, using an external magnet, and could be reused several times without significant loss of activity under the optimum reaction conditions.
Microwave-promoted cross-coupling of acid chlorides with arylboronic acids: a convenient method for preparing aromatic ketones
Polá?ková, Viera,Toma, ?tefan,Augustínová, Iveta
, p. 11675 - 11678 (2006)
Simple catalytic systems for cross-coupling reactions of acyl chlorides with arylboronic acids under microwave conditions were tested. Microwave irradiation facilitated the reaction course. Mild reaction conditions afford the symmetrical and unsymmetrical aryl ketones in reasonable to high yields within a short time. A wide range of substrates bearing an electron-donating or an electron-withdrawing substituent on aryl ring of acid chloride as well as on boronic acid were examined and high yields of ketones were produced.
Ruthenium(III)-catalyzed mechanistic studies of oxidation of benzhydrols by sodium N-chloro-p-toluenesulfonamide in HCl medium
Ramachandra,Mahadevappa,Rangappa,Gowda
, p. 773 - 780 (1997)
The reaction rate of the ruthenium(III)-catalyzed oxidation of benzyhydrol and its derivatives by sodium N-chloro-p-toluenesulfonamide or chloramine-T (CAT) in the presence of hydrochloric acid in 30% (v/v) MeOH medium was determined at 35 °C. The reaction rate showed a first-order dependence on [CAT]o and a fractional-order each on [YBH]o [Ru(III)], and [H+]. The reaction rate also has a negative fractional-order behavior in the reduction product of CAT and p-toluenesulfonamide.
REACTIONS OF ORGANOMETALLIC COMPOUNDS, CATALYZED BY TRANSITION METAL COMPLEXES. 8. CARBONYLATION OF ARYLMERCURY COMPOUNDS IN THE PRESENCE OF PALLADIUM AND RHODIUM
Bumagin, N.A.,Kalinovskii, I.O.,Beletskaya, I.P.
, p. 2368 - 2373 (1984)
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Carbonylative Suzuki-Miyaura Coupling Reactions of Aryl Iodides with Readily Available Polymer-Immobilized Palladium Nanoparticles
Yasukawa, Tomohiro,Zhu, Zhiyuan,Yamashita, Yasuhiro,Kobayashi, Shu
, p. 502 - 504 (2021)
Polysilane/alumina-supported palladium nanoparticle catalyzed carbonylative Suzuki-Miyaura coupling reactions under ligand-free conditions have been developed to synthesize diaryl ketones. High yields and selectivities were achieved even with low catalyst loading under atmospheric pressure of CO gas. A variety of aryl iodides and arylboronic acids could be utilized to afford the diaryl ketones in excellent yields. Moreover, the ligand-free immobilized palladium nanoparticles could be recovered by simple filtration and the catalytic activity could be maintained for several runs.
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Baumann,J.B.
, p. 396 - 398 (1971)
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Synthesis of biaryl ketones and biaryl diketones via carbonylative Suzuki-Miyaura coupling reactions catalyzed by bridged bis(N-heterocyclic carbene)palladium(II) catalysts
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Page/Page column 20; 22-26, (2021/12/23)
This disclosure relates to bridged bis(N-heterocyclic carbene)palladium(II) complexes, methods of preparing the complexes, and methods of using the complexes in Suzuki-Miyaura coupling reactions.
Synthesis and application of SBA-Pr-Py@Pd in Suzuki-type cross-coupling reaction
Mohammadi Ziarani, Ghodsi,Ebrahimi, Zahra,Mohajer, Fatemeh,Badiei, Alireza
, p. 4583 - 4594 (2021/08/06)
SBA-Pr-Py was synthesized by functionalization of SBA-15 with 4-pyridine carbaldehyde, and then it was grafted by palladium ions to give SBA-Pr-Py@Pd nanocatalyst, which was used in cross-coupling reaction. In this process, aryl boronic acid is treated with various acyl halides using SBA-Pr-Py@Pd catalyst to provide aryl ketones under mild conditions. Graphical abstract: [Figure not available: see fulltext.].
