- Synthesis of Isoselenazoles and Isothiazoles from Demethoxylative Cycloaddition of Alkynyl Oxime Ethers
-
A general method for the synthesis of isoselenazoles and isothiazoles has been developed by the base-promoted demethoxylative cycloaddition of alkynyl oxime ethers using the cheap and inactive Se powder and Na2S as selenium and sulfur sources. This transformation features the direct construction of N-, Se-, and S-containing heterocycles through the formation of N-Se/S and C-Se/S bonds in one-pot reactions with excellent functional group tolerance.
- Zhang, Zhu-Zhu,Chen, Rong,Zhang, Xiao-Hong,Zhang, Xing-Guo
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p. 632 - 642
(2020/12/22)
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- Feeding Carbonylation with CO2via the Synergy of Single-Site/Nanocluster Catalysts in a Photosensitizing MOF
-
Solar-driven carbonylation with CO2 replacing toxic CO as a C1 source is of considerable interest; however it remains a great challenge due to the inert CO2 molecule. Herein, we integrate cobalt single-site and ultrafine CuPd nanocluster catalysts into a
- Fu, Shanshan,Guo, Guang-Chen,Guo, Song,Lu, Tong-Bu,Yao, Shuang,Yuan, Wenjuan,Zhang, Zhi-Ming
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p. 20792 - 20801
(2021/12/14)
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- Electrochemical Palladium-Catalyzed Oxidative Sonogashira Carbonylation of Arylhydrazines and Alkynes to Ynones
-
Oxidative carbonylation using carbon monoxide has evolved as an attractive tool to valuable carbonyl-containing compounds, while mixing CO with a stoichiometric amount of a chemical oxidant especially oxygen is hazardous and limits its application in scale-up synthesis. By employing anodic oxidation, we developed an electrochemical palladium-catalyzed oxidative carbonylation of arylhydrazines with alkynes, which is regarded as an alternative supplement of the carbonylative Sonogashira reaction. Combining an undivided cell with constant current mode, oxygen-free conditions avoids the explosion hazard of CO. A diversity of ynones are efficiently obtained using accessible arylhydrazines and alkynes under copper-free conditions. A possible mechanism of the electrochemical Pd(0)/Pd(II) cycle is rationalized based upon cyclic voltammetry, kinetic studies, and intermediates experiments.
- Cao, Yue,Hu, Jingcheng,Lei, Aiwen,Li, Haoran,Shi, Renyi,Wu, Yong,Xu, Minghao,Yi, Hong,Zeng, Li
-
supporting information
p. 12460 - 12466
(2021/08/24)
-
- One-Pot Palladium-Catalyzed Carbonylative Sonogashira Coupling using Carbon Dioxide as Carbonyl Source
-
Carbonylation coupling reaction has emerged as a powerful and versatile strategy for the construction of carbonyl-containing compounds in modern synthetic chemistry over the past years. Carbon dioxide, a renewable one carbon molecule, has become one of the most attractive and promising alternative carbonyl sources due to its highly abundance, nontoxicity and stability in comparison with CO in recent years. However, in most cases, a two-chamber technique was generally necessary to allow the CO-producing and CO-consuming processes to perform successfully because of the complexities and incompatibility of reaction conditions, when carbon dioxide was utilized as carbonyl source. Herein, a practical one-pot protocol using carbon dioxide as the carbonyl source for the palladium-catalyzed carbonylative Sonogashira coupling has been established, providing an expedient and practical route to a wide range of functionalized alkynones and indoxyls under mild reaction conditions. By finding a suitable catalytic system, the method allowed the CO-generating and CO-consuming processes to proceed in one pot, wherein carbon monoxide was generated in situ from the reduction of carbon dioxide in the absence of any fluoride reagents. Simple and safe operation, readily available substrates, good functional group tolerance and mild reaction conditions are the features of the method.
- Xiong, Wenfang,Wu, Bowen,Zhu, Baiyao,Tan, Xiaobin,Wang, Lu,Wu, Wanqing,Qi, Chaorong,Jiang, Huanfeng
-
p. 2843 - 2851
(2021/05/10)
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- Atom-Economic Synthesis of Highly Functionalized Bridged Ring Systems Initiated by Ring Expansion of Indene-1,3-dione
-
An atom economic procedure for the regioselective synthesis of bridged seven-membered-ring compounds from simple reactants such as ynones and indene-1,3-dione has been developed. This process was realized through the one-pot reactions of ring-expansion of
- Mu, Yuanyang,Yao, Qiyi,Yin, Liqiang,Fu, Siyi,Wang, Mengdan,Yuan, Yang,Kong, Lingkai,Li, Yanzhong
-
p. 6755 - 6764
(2021/05/06)
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- Solvent switchable Pd/DNA catalyst in carbonylative Sonogashira coupling
-
Palladium catalysts immobilized on DNA (Pd/DNA) were applied for the first time in the carbonylative Sonogashira coupling, at 1 atm of CO. Different alkynones were obtained with a high yield in DMF. In the presence of water, the selectivity completely changed and diaryl alkynes, typical Sonogashira products, were selectively formed. In addition to Pd/DNA, soluble palladium species also participated in the catalytic process. The stability of the catalytic system increased after the addition of DNA excess.
- Mart, M.,Trzeciak, A. M.
-
-
- Visible-light-mediated photocatalytic cross-coupling of acetenyl ketones with benzyl trifluoroborate
-
In this report, we describe a simple visible light-triggered Barbier-type reaction by employing acetenyl ketones with benzyl trifluoroborates. Through a radical-radical cross-coupling process, this photocatalytic protocol furnished a wide range of tertiary propargyl alcohols. Mechanistic investigation indicated that proton-coupled electron transfer (PCET) might be involved in the photochemical transformations.
- Zhang, Lingchun,Chu, Yanle,Ma, Peizhi,Zhao, Shujuan,Li, Qiaoyan,Chen, Boya,Hong, Xuejiao,Sun, Jun
-
supporting information
p. 1073 - 1077
(2020/02/22)
-
- Selective Insertion of Alkynes into C-C σ Bonds of Indolin-2-ones: Transition-Metal-Free Ring Expansion Reactions to Seven-Membered-Ring Benzolactams or Chromone Derivatives
-
An unprecedented ring expansion reaction of indolin-2-ones with alkynyl ketones under transition-metal-free conditions has been developed. Base-promoted selective cleavage of a C-C σ bond of the amide is the key in this process, which provides a straightf
- Wang, Mengdan,Yang, Yajie,Song, Bo,Yin, Liqiang,Yan, Shuhui,Li, Yanzhong
-
p. 155 - 159
(2020/01/03)
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- Recyclable heterogeneous palladium-catalyzed carbonylative Sonogashira coupling under CO gas-free conditions
-
A convenient, efficient and practical heterogeneous palladium-catalyzed carbonylative Sonogashira coupling of aryl iodides with terminal alkynes under CO gas-free conditions has been developed by using an MCM-41-supported bidentate phosphine palladium ace
- Zhou, Zebiao,Li, Jianying,Xu, Zhaotao,Cai, Mingzhong
-
supporting information
p. 2015 - 2025
(2020/05/13)
-
- Copper-catalyzed method for preparing aldehyde or ketone compound by oxidizing alcohol with oxygen as oxidizing agent and application
-
The invention discloses a copper-catalyzed method for preparing an aldehyde or ketone compound by oxidizing alcohol with oxygen as an oxidizing agent. Reaction is performed in an organic solvent for 4-48 hours at room temperature by using copper salt and nitroxide free radicals as catalysts and oxygen or air as an oxidizing agent to efficiently oxidize an alcohol compound into the corresponding aldehyde or ketone compound. The method is simple to operate, free of chlorides corrosive to equipment, available in raw materials and reagents, mild in reaction conditions, wide in substrate universality, good in functional group compatibility, convenient in separation and purification, environmentally friendly in the whole process and free of pollution, and is a method suitable for industrial production.
- -
-
Paragraph 0028-0030; 0124-0129
(2020/08/18)
-
- Pyrene marked benzimidazole n-heterocyclic carbene palladium metal complex and preparation and application thereof
-
The invention relates to a pyrene marked benzimidazole n-heterocyclic carbene palladium metal complex. The pyrene marked benzimidazole n-heterocyclic carbene palladium metal complex is prepared from benzimidazole serving as a skeleton and pyridine serving
- -
-
Paragraph 0106; 0107; 0108
(2019/06/11)
-
- Synthesis of 1-Cyano-3-acylnaphthalenes via Formal [4+2] Benzannulation of 2-(2-Alkynylphenyl)acetonitriles and Alkynones
-
Effective transition-metal-free formal [4+2] benzannulation for the preparation of 1-cyano-3-acylnaphthalenes from 2-(2-alkynylphenyl)acetonitriles and alkynones through sequential C-C bond coupling has been developed. This protocol is characterized by mi
- Chen, Lu-Lu,Zhang, Jing-Wen,Yang, Wan-Wan,Fu, Ji-Ya,Zhu, Jun-Yan,Wang, Yan-Bo
-
p. 8090 - 8099
(2019/06/27)
-
- Base-Controlled Divergent Synthesis of 5-Cyanobenzoxepines and Benzofuro[2,3- b]pyridines from 2-Bromophenylacetonitriles and Ynones
-
An effective base-controlled divergent annulation reaction of 2-bromophenylacetonitriles and ynones has been developed. Various functionalized 5-cyanobenzoxepines and benzofuro[2,3-b]pyridines were obtained with a broad substrate scope and high regioselec
- Chen, Lu-Lu,Zhang, Jing-Wen,Chen, Pei,Zhang, Shuai,Yang, Wan-Wan,Fu, Ji-Ya,Zhu, Jun-Yan,Wang, Yan-Bo
-
supporting information
p. 5457 - 5461
(2019/08/01)
-
- Synthesis of α,β-alkynyl ketones via the nickel catalysed carbonylative Sonogashira reaction using oxalic acid as a sustainable C1 source
-
An efficient and economic nickel-dppb catalyzed, carbonylative Sonogashira cross-coupling reaction was demonstrated to provide rapid access to various α,β-alkynyl ketones from aryl iodides and terminal alkynes using oxalic acid as the ex situ C1 source in a double vial (DV) system. Notably, the role of the ligand in combination with the Ni catalyst for the selective formation of carbonylative Sonogashira products was investigated and supported with control experiments. Yet, no reports are available for carbonylative Sonogashira coupling by using a CO-surrogate under Ni-catalyzed conditions. In this process, for the first time, oxalic acid is used as an ex situ solid, bench stable, easy to handle and efficient CO surrogate in a DV-system for the carbonylative Sonogashira coupling reaction with vast substrate scope.
- Shaifali,Ram, Shankar,Thakur, Vandna,Das, Pralay
-
supporting information
p. 7036 - 7041
(2019/08/01)
-
- N-heterocyclic carbene palladium complex crystal and synthetic method thereof and application of n-heterocyclic carbene palladium complex crystal in preparation of alpha,beta-unsaturated ketone compounds
-
The invention discloses an n-heterocyclic carbene palladium complex crystal and a synthetic method thereof and application of the n-heterocyclic carbene palladium complex crystal in preparation of alpha,beta-unsaturated ketone compounds. A structural form
- -
-
Paragraph 0029-0034[ 0067-0070
(2019/11/28)
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- Carbonylative Sonogashira Coupling of Aryl Iodides with Terminal Alkynes Catalyzed by Palladium Nanoparticles
-
A convenient and efficient method for the synthesis of α,β-alkynyl ketones from the three-component coupling of aryl iodides, terminal alkynes, and carbon monoxide (carbonylative Sonogashira coupling reaction) is successfully developed. The carbonylative Sonogashira coupling reaction proceeded smoothly under mild conditions in the presence of palladium nanoparticles to produce the corresponding α,β-alkynyl ketones in good to excellent yields.
- Feng, Xiujuan,Song, Jiliang,Bao, Ming
-
p. 337 - 345
(2017/11/27)
-
- An effective preparation of both 1,3-diketones and nitriles from alkynones with oximes as hydroxide sources
-
An effective phosphine-catalyzed protocol has been established for the syntheses of 1,3-diketones and nitriles from alkynones with oximes as hydroxide surrogates. This method features the use of a phosphine catalyst, compatibility with various functional groups and ambient temperature, which makes this approach very practical. A plausible mechanism was proposed.
- Chen, Pei,Zhang, Qian-Qian,Guo, Jia,Chen, Lu-Lu,Wang, Yan-Bo,Zhang, Xiao
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p. 6958 - 6966
(2018/10/02)
-
- Cycloaddition Reaction of α,β-Alkynic Hydrazones and KSCN under Transition-Metal-Free Conditions: Synthesis of N-Iminoisothiazolium Ylides
-
A novel heteroannulation reaction between α,β-alkynic hydrazones and potassium thiocyanate has been developed for the synthesis of N-iminoisothiazolium ylides. The transformation features wide substrate scope, functional tolerance, and easy operation. This investigation involves a [4 + 1]-type cycloaddition reaction and C-S/S-N bond formation under transition-metal-free conditions. The application of this transformation to the gram-scale preparation of the N-imide ylide is also accomplished.
- Liu, Bei-Bei,Cao, Wen-Bin,Wang, Fei,Wang, Shun-Yi,Ji, Shun-Jun
-
supporting information
p. 11118 - 11124
(2018/09/06)
-
- Silver-catalyzed Double Decarboxylative Radical Alkynylation/Annulation of Arylpropiolic Acids with α-keto Acids: Access to Ynones and Flavones under Mild Conditions
-
Ynones are privileged building blocks in various organic syntheses of heterocyclic derivatives due to their multifunctional nature, and flavones are an important class of natural products with a wide range of biological activities. We describe the catalytic double decarboxylative alkynylation of arylpropiolic acids with α-keto acids. With Ag(I)/persulfate as the catalysis system, the valuable ynones bearing various substituents could be easily obtained. The introduction of hydroxyl substituent on ortho-site of α-keto acids make this strategy further applicable to the construction of flavone derivatives via heteroannulation in moderate to good yields with a similar silver-catalyzed system. The reactions proceed under relatively mild reaction conditions and tolerate a wide variety of functional groups. Control experiments indicated that both the reactions undergo radical processes. (Figure presented.).
- Meng, Mengting,Wang, Guofang,Yang, Liangfeng,Cheng, Kai,Qi, Chenze
-
supporting information
p. 1218 - 1231
(2018/02/16)
-
- Transition-Metal-Free Ring Expansion Reactions of Indene-1,3-dione: Synthesis of Functionalized Benzoannulated Seven-Membered Ring Compounds
-
A novel ring expansion reaction of indene-1,3-dione with alkynyl ketones under transition-metal-free conditions has been developed. This process offers an efficient and direct way to synthesize benzoannulated seven-membered rings or fused-ring compounds t
- Yao, Qiyi,Kong, Lingkai,Wang, Mengdan,Yuan, Yang,Sun, Ruizhuo,Li, Yanzhong
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p. 1744 - 1747
(2018/04/14)
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- Method for preparing acetyenic ketone compound by using B-form DNA to promote Sonogashira reaction
-
The invention discloses a method for preparing an acetyenic ketone compound by using B-form DNA to promote Sonogashira reaction. According to the method, the B-form DNA is used as an accelerant, purewater is used as a solvent, potassium carbonate is taken
- -
-
Paragraph 0014; 0052; 0053; 0054
(2018/09/08)
-
- A polysalen based on polyacylamide stabilized palladium nanoparticle catalyst for efficient carbonylative Sonogashira reaction in aqueous media
-
A highly cross-linked polymer matrix polysalen based on acrylamide and N,N'-methylene-bisacrylamide (NNMBA) was successfully prepared. It has been proved that this type of polysalen is an effective support for immobilizing palladium complex. The polysalen may provide coordination sites for conjugation with a palladium catalyst to produce polysalen-Pd catalyst. The polysalen-Pd was firstly applied in phosphine-free carbonylative Sonogashira coupling reactions of aryl iodides with terminal alkynes to produce α,β-alkynyl ketones in 81-95% yields in aqueous media, which was much higher than that of homogeneous Pd-salen in 52% yield. Furthermore, the catalyst showed excellent recyclability without any significant loss in its activity.
- Wang, Yan,Yang, Xiaolong,Yu, Jianqiang
-
p. 31850 - 31857
(2017/07/10)
-
- A Convenient and Efficient Palladium-Catalyzed Carbonylative Sonogashira Transformation with Formic Acid as the CO Source
-
A practical, convenient, and efficient palladium-catalyzed carbonylative Sonogashira reaction of aryl iodides was developed. With formic acid as the CO source and dicyclohexylcarbodiimide as the activator, various alkynones were produced in good to excell
- Peng, Jin-Bao,Wu, Fu-Peng,Li, Chong-Liang,Qi, Xinxin,Wu, Xiao-Feng
-
supporting information
p. 1434 - 1437
(2017/04/01)
-
- Synthesis of Fluorescent 1,3-Diarylpropynones by Carbonylative Alkynylation Reaction Using (Phosphine) (1,2,3-triazol-5-ylidene)palladium Complexes as Catalysts
-
The synthesis of a variety of 1,3-diarylpropynones that contain not only substituted phenyl groups but also fluorophoric 1-pyrenyl, 3-carbazolyl, and 1-naphthyl groups was achieved in good to excellent yields by using a carbonylative alkynylation reaction in the presence of cis-(Tz)Pd(Cl)2(PPh3) (Tz = 1,2,3-triazol-5-ylidene) as a precatalyst under 1.0 atm of CO. Products resulting from competing Sonogashira coupling reactions, namely 1,2-diarylacetylenes, were not observed. The synthesized ynones exhibit fluorescence not only in solution but also in the solid state. The catalytically active palladium species was recovered and reused for up to three cycles by adsorbing the cis-(Tz)Pd(Cl)2(PPh3) precatalyst onto silica gel and carrying out the reaction under heterogeneous conditions.
- Dasgupta, Ayan,Ramkumar, Venkatachalam,Sankararaman, Sethuraman
-
supporting information
p. 4817 - 4823
(2016/10/13)
-
- Carboxylic acid [...]end alkyne couplingacetylenic ketone the method of preparation
-
The invention discloses a method for preparing acetyenic ketone by coupling carboxylate triazinyl ester with terminal alkyne. According to the method, palladium acetate is taken as a catalyst, and a carboxylate triazinyl ester compound is taken as an elec
- -
-
Paragraph 0014-0017; 0129
(2016/11/21)
-
- Palladium anchored on amine-functionalized K10 as an efficient, heterogeneous and reusable catalyst for carbonylative Sonogashira reaction
-
The present work describes the immobilization of palladium chloride (II) on the amine functionalized K10 support and its application toward the carbonylative Sonogashira reactions. The various catalyst characterization techniques revealed the successful grafting of APTES moiety on the K10 clay surface through covalent bonding and Pd with the NH2 groups of APTES@K10 through co-ordinate bonding. The immobilized catalyst was successively applied for copper and phosphine free carbonylative Sonogashira reaction of aryl and hetero aryl iodides with terminal alkynes. To our delight, the electron withdrawing aryl halides can be efficiently utilized as an electrophiles giving higher selectivity toward carbonylated products. Moreover, dibenzoylmethane which is a potential synthetic intermediate in organic transformation has been also synthesized using this protocol. Recovery of catalyst by simple filtration and its reuse up to four consecutive cycles ensure the robustness of present catalytic protocol.
- Chavan, Sujit P.,Varadwaj, G.Bishwa Bidita,Parida, Kulamani,Bhanage, Bhalchandra M.
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p. 237 - 245
(2015/10/12)
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- Bifunctional ligands in combination with phosphines and Lewis acidic phospheniums for the carbonylative Sonogashira reaction
-
The combination of phosphine-ligated Pd catalysis and phosphenium(v) Lewis acid catalysis has been developed for the carbonylative Sonogashira reaction using phosphino-phosphenium salts (L1-L4) as bifunctional ligands, in which the Lewis acidic phospheniu
- Tan, Chen,Wang, Peng,Liu, Huan,Zhao, Xiao-Li,Lu, Yong,Liu, Ye
-
supporting information
p. 10871 - 10874
(2015/06/30)
-
- Privilege Ynone Synthesis via Palladium-Catalyzed Alkynylation of "Super-Active Esters"
-
A neat palladium-catalyzed alkynylation reaction was developed with "super-active ester" as the carbonyl electrophile, which provides a clean and efficient synthetic protocol for a broad array of ynone compounds under CO-, Cu-, ligand-, and base-free conditions. The superior activity of triazine ester was rationalized by the strong electron-withdrawing ability and the unique affinity of triazine on palladium. A mechanistic experiment clearly demonstrated that the N-Pd coordination of triazine plays a crucial role for the highly efficient C-O activation. (Chemical Equation presented).
- Yu, Bo,Sun, Huaming,Xie, Zunyuan,Zhang, Guofang,Xu, Li-Wen,Zhang, Weiqiang,Gao, Ziwei
-
supporting information
p. 3298 - 3301
(2015/07/15)
-
- Dual-immobilized copper catalyst: Carbon nitride-supported copper nanoparticles catalyzed oxidation of propargylic alcohols
-
Copper nanoparticles were supported and modified by carbon nitride, which was utilized as support and might work as a kind of immobilized N-donor ligand. The modified nanoparticle catalyst was evaluated with the oxidation of propargylic alcohols and showed highly catalytic efficiency as well as significant ligand or support effect in the reaction. The dual-immobilized nanoparticle catalyst could be recycled for 3 times at least without an obvious decrease in catalytic activities.
- Lv, Wei,Tian, Jing,Deng, Nan,Wang, Yan,Zhu, Xiaoshu,Yao, Xiaoquan
-
supporting information
p. 1312 - 1316
(2015/03/04)
-
- Carbonylative Sonogashira coupling of terminal alkynes with aryl iodides under atmospheric pressure of CO using Pd(II)@MOF as the catalyst
-
A novel, highly efficient, and phosphine-free heterogeneous palladium-MOF catalytic system for the carbonylative Sonogashira coupling of terminal alkynes with aryl iodides was developed. The catalyst could efficiently promote the carbonylative coupling reaction under atmospheric pressure of CO, affording the corresponding aryl α,β-alkynyl ketones in good to excellent yields. Besides high activity and selectivity, the proposed catalytic system features a broad substrate scope for both alkynes and aryl iodides. Moreover, the heterogeneous catalyst was recyclable, showed negligible metal leaching, and could be reused at least five times without significant loss in catalytic efficiency under the investigated conditions. the Partner Organisations 2014.
- Bai, Cuihua,Jian, Siping,Yao, Xianfang,Li, Yingwei
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p. 3261 - 3267
(2014/08/18)
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- Recyclable and reusable PdCl2(PPh3) 2/PEG-2000/H2O system for the carbonylative Sonogashira coupling reaction of aryl iodides with alkynes
-
PdCl2(PPh3)2 in a mixture of water and poly(ethylene glycol) (PEG-2000) is shown to be an extremely active catalyst for the carbonylative Sonogashira coupling reaction of aryl iodides with terminal alkynes. The reaction can be conducted under an atmospheric pressure of carbon monoxide at 25 °C with Et3N as a base, yielding a variety of alkynyl ketones in good to excellent yields. Application of this synthetic method to prepare flavones from o-iodophenol and terminal alkynes was also achieved. The isolation of the products is readily achieved by extraction with diethyl ether, and the PdCl2(PPh3)2/PEG-2000/ H2O system can be easily recycled and reused six times without any loss of catalytic activity. the Partner Organisations 2014.
- Zhao, Hong,Cheng, Mingzhu,Zhang, Jiatao,Cai, Mingzhong
-
supporting information
p. 2515 - 2522
(2014/05/06)
-
- Aryl-palladium-NHC complex: Efficient phosphine-free catalyst precursors for the carbonylation of aryl iodides with amines or alkynes
-
A series of aryl-palladium-NHC compounds was prepared according to the reported methods and their catalytic activity in the carbonylation of aryl iodides to synthesize α-keto amides and alkynones was examined. These practical aryl-palladium-NHC complexes have shown highly efficient catalyzed carbonylation and Sonogashira carbonylation reactions, with high turnover number in synthesis of α-keto amides (TON = 4300) and in synthesis of alkynones (TON = 980).
- Zhang, Chunyan,Liu, Jianhua,Xia, Chungu
-
supporting information
p. 9702 - 9706
(2015/02/19)
-
- Gold-catalyzed 1,3-transposition of ynones
-
An efficient, regioselective gold-catalyzed 1,3-transposition reaction of ynones and diynones has been developed. It was found that stereoelectronic (interrupted conjugation) and electronic (extended conjugation) factors could efficiently govern the regio
- Kazem Shiroodi, Roohollah,Soltani, Mohammad,Gevorgyan, Vladimir
-
supporting information
p. 9882 - 9885
(2014/08/05)
-
- Palladium nanoparticles supported on Smopex metal scavengers as catalyst for carbonylative Sonogashira reactions: Synthesis of α,β-alkynyl ketones
-
Palladium nanoparticles supported on two Smopex commercial metal scavengers (1% w/w) have been tested in the carbonylative Sonogashira reactions of aryl iodides with phenylacetylene. Their catalytic activity has been compared with those of more common catalysts (Pd/C, Pd/γ-Al 2O3). Pd/Smopex-234 resulted especially effective in the synthesis of alkynyl ketones even working with a low amount of palladium (0.2-0.5 mol%). Preliminary heterogeneity tests (i.e. hot filtration test, Pd leaching and recycle of the catalyst) have been performed in order to evaluate the catalytic behaviour of this system. The obtained results seem to indicate that Pd/Smopex-234 could act as a truly heterogeneous catalyst.
- Aronica, Laura Antonella,Caporusso, Anna Maria,Tuci, Giulia,Evangelisti, Claudio,Manzoli, Maela,Botavina, Maria,Martra, Gianmario
-
-
- Cross-linked polymer supported palladium catalyzed carbonylative Sonogashira coupling reaction in water
-
A cross-linked polymer-supported ionic liquid immobilized palladium catalyst, which is prepared by reaction of the Pd(OAc)2 with copolymer of 3-butyl-1-vinylimidazolium iodide and divinylbenzene, was well characterized and employed as an effective heterogeneous catalyst for carbonylative Sonogashira coupling reaction of aryl iodides with terminal alkynes in water, affording the corresponding α,β-alkynyl ketones in good to excellent yields. The catalytic system not only solves the basic problem of homogeneous palladium catalyst recovery and reuse but also avoids the use of toxic phosphine ligands. The stability of supported palladium was also discussed.
- Wang, Yan,Liu, Jianhua,Xia, Chungu
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experimental part
p. 1587 - 1591
(2011/04/26)
-
- A supported palladium nanocatalyst for copper free acyl Sonogashira reactions: One-pot multicomponent synthesis of N-containing heterocycles
-
A convenient method has been developed for the synthesis of palladium nanoparticles (PdNPs) embedded into a polymer matrix, PPS [PPS = poly(1,4-phenylene sulfide)], via the thermolysis of palladium acetate. X-ray photoelectron spectroscopy (XPS) studies c
- Santra, Subhankar,Dhara, Kalyan,Ranjan, Priyadarshi,Bera, Parthasarathi,Dash, Jyotirmayee,Mandal, Swadhin K.
-
supporting information; experimental part
p. 3238 - 3247
(2011/12/15)
-
- Pd-catalyzed carbonylative reactions of aryl iodides and alkynyl carboxylic acids via decarboxylative couplings
-
Alkynyl carboxylic acids reacted with aryl iodides under a CO atmosphere in the presence of a palladium catalyst to produce α,β-alkynyl aryl ketones in good yields. The maximum turnover number was 16 800. The desired carbonylative coupling was formed from phenyl propiolic acid without any formation of a noncarbonylative coupling product in the absence of CuI. However, the reaction with alkyl-substituted alkynyl carboxylic acids required CuI as a cocatalyst for high yield.(Figure Presented)
- Park, Ahbyeol,Park, Kyungho,Kim, Yong,Lee, Sunwoo
-
supporting information; experimental part
p. 944 - 947
(2011/04/24)
-
- A general palladium-catalyzed carbonylative sonogashira coupling of aryl triflates
-
Trifling with triflates: A new protocol for the carbonylative Sonogashira reactions of aryl triflates (see scheme) that provides a significant extension of this interesting methodology is described.
- Wu, Xiao-Feng,Sundararaju, Basker,Neumann, Helfried,Dixneuf, Pierre H.,Beller, Matthias
-
supporting information; experimental part
p. 106 - 110
(2011/03/19)
-
- Ligand-promoted, copper nanoparticles catalyzed oxidation of propargylic alcohols with TBHP or Air as Oxidant
-
A highly efficient oxidation of propargylic alcohols to ynones was catalyzed by copper nanoparticles (Cu Nps) with TBHP as an oxidant at room temperature. With bipyridine as the ligand, the reaction was accelerated significantly and led in good to excellent yields to a variety of propargylic alcohols. Furthermore, with Cu Nps as the catalyst, molecular oxygen in air could be utilized as oxidant effectively in the presence of bpy ligand. Georg Thieme Verlag Stuttgart - New York.
- Han, Chengyan,Yu, Min,Sun, Weijiang,Yao, Xiaoquan
-
experimental part
p. 2363 - 2368
(2011/10/30)
-
- Synthesis of phosphonylated and thiolated indenones by manganese(III)- mediated addition of phosphorus- and sulfur-centered radicals to 1,3-diarylpropynones
-
Phosphorus- or sulfur-centered radicals generated from the reaction of manganese(III) acetate with dialkyl phosphonates or arylthiols undergo selective additions to conjugated alkynes followed by cyclization and rearomatization to afford 2-phosphonyl- or
- Zhou, Jun,Zhang, Guang-Liang,Zou, Jian-Ping,Zhang, Wei
-
supporting information; experimental part
p. 3412 - 3415
(2011/09/12)
-
- Magnetically separable Pd catalyst for carbonylative sonogashira coupling reactions for the synthesis of α,β-alkynyl ketones
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(Chemical Equation Presented) A magnetically separable palladium catalyst was simply synthesized through a wet impregnation incorporating palladium nanoparticles and superparamagnetic Fe3O4 nanoparticles in KBH4 solution,
- Liu, Jianming,Peng, Xingao,Sun, Wei,Zhao, Yongwei,Xia, Chungu
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supporting information; experimental part
p. 3933 - 3936
(2009/05/30)
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- A simple and efficient recyclable phosphine-free catalytic system for alkoxycarbonylation and carbonylative Sonogashira coupling reactions of aryl iodides
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Using palladium on charcoal (Pd/C) and triethylamine as a novel, efficient, versatile, recyclable, and phosphine-free catalytic system, we carried out the alkoxycarbonylation of aryl iodides (alcohols or phenols as nucleophiles) and the carbonylative Sonogashira coupling reaction of aryl iodides with terminal alkynes, affording the corresponding aryl esters and α, β-alkynyl ketones in good to excellent yields under mild conditions. We found that both electron-withdrawing and electron-donating substituents on phenol enhanced the phenoxycarbonylation of iodobenzene. The recyclability of Pd/C was also demonstrated.
- Liu, Jianhua,Chen, Jing,Xia, Chungu
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- Cobalt(III) complex catalyzed aerobic oxidation of propargylic alcohols
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An o-phenylenebis(N′-methyloxamidate) cobalt(III) complex works as an efficient catalyst for the oxidation of propargylic alcohols to the corresponding α,β-acetylenic carbonyl compounds, in the presence of pivalaldehyde, under an atmospheric pressure of m
- Blay, Gonzalo,Cardona, Luz,Fernandez, Isabel,Pedro, Jose R.
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p. 3329 - 3332
(2008/09/21)
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- Synthesis of acetylenic ketones by a Pd-catalyzed carbonylative three-component coupling reaction in [bmim]PF6
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A carbonylative three-component coupling reaction of aryl iodides with terminal alkynes catalyzed by PdCl2(PPh3)2 was carried out using an ionic liquid, [bmim]PF6, as the reaction medium, which resulted in good yields of α,β-acetylenic ketones. The low-viscosity ionic liquid, [bmim]NTf2, was not suitable for this reaction, since the background Sonogashira coupling reaction, a competing reaction, also proceeded.
- Fukuyama, Takahide,Yamaura, Ryo,Ryu, Ilhyong
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p. 711 - 715
(2007/10/03)
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- Aqueous ammonia as a new activator for Sonogashira coupling
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Sonogashira coupling, which is a coupling reaction of terminal alkynes with organic halides, takes place with dilute aqueous ammonia as an activator. The reaction of several terminal alkynes and aryl iodides in the presence of small excess of aqueous ammonia at room temperature furnishes the cross-coupling product in good-to-excellent yields. A water-soluble amine with a high boiling point is alternatively employed for reactions at higher temperatures. A related coupling reaction in the presence of carbon monoxide also proceeded at room temperature and under ambient pressure to afford α,β-alkynyl ketones efficiently.
- Mohamed Ahmed, Mohamed S.,Sekiguchi, Akitoshi,Masui, Kentaro,Mori, Atsunori
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p. 160 - 168
(2007/10/03)
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- Carbonylative Sonogashira coupling of terminal alkynes with aqueous ammonia
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(Matrix presented) Carbonylative coupling of phenylethyne with 4-methoxy-1-iodobenzene in the presence of 1 mol% PdCl2(PPh 3)2, 2 equiv of 0.5 M aqueous ammonia, and CO (1 atm) gives the corresponding α,β-alkynyl ketone in
- Mohamed Ahmed, Mohamed S.,Mori, Atsunori
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p. 3057 - 3060
(2007/10/03)
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- A convenient synthesis of conjugated acetylenic ketones by copper(I)-catalysis under microwave irradiation
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A rapid and efficient synthesis of conjugated acetylenic ketones is reported involving copper(I)-catalysed aroylation of phenylacetylene with aroyl chloride under microwave irradiation.
- Wang,Wei,Hu,Liua,Kang
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p. 146 - 147
(2007/10/03)
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- Microwave-assisted coupling reaction by copper(I)-catalyzed of terminal alkynes with aroyl chlorides
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A rapid and efficient method for synthesis of α,β-conjugated acetylenic ketones involves reaction of phenylacetylene with aroyl chlorides in the presence of catalytic amount CuI under microwave irradiation to give the corresponding α,β-conjugated acetylen
- Wang,Wei,Hu,Liu,Fu
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p. 3527 - 3532
(2007/10/03)
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- A facile synthesis of conjugated acetyl ketones by Pd(II)-Cu(I) doped KF/Al2O3-catalyzed under microwave irradiation
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A rapid and efficient method for synthesis of α,β-conjugated acetylenic ketones involves reaction of phenylacetylene with aroyl chlorides in the presence of a catalytic amount Pd(PPh3)2Cl2-CuI doped KF/Al2O
- Wang,Wei,Huang,Hu,Bai
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p. 3337 - 3343
(2007/10/03)
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