42495-51-2Relevant academic research and scientific papers
Transition-Metal-Free Regiospecific Aroylation of Nitroarenes Using Ethyl Arylacetates at Room Temperature
Kumar, Promod,Sharma, Anup Kumar,Guntreddi, Tirumaleswararao,Singh, Rahul,Singh, Krishna Nand
supporting information, p. 744 - 747 (2018/02/09)
A novel regiospecific C(sp3)-C(sp2) coupling between ethyl arylacetates and nitroarenes has been developed to deliver biaryl ketones in excellent yields. The protocol is metal-free, mild, and compatible with a number of functional groups on both of the reacting partners.
Transition metal-free Suzuki type cross-coupling reaction for the synthesis of dissymmetric ketones
Jadhav, Sanjay,Rashinkar, Gajanan,Salunkhe, Rajashri,Kumbhar, Arjun
supporting information, p. 3201 - 3204 (2017/07/27)
A simple, efficient and metal-free route for the synthesis of dissymmetric ketones through Suzuki type cross-coupling reaction has been established. This strategy signifies an attractive, cost-effective and operationally convenient tool for the synthesis of a wide range of dissymmetric ketones. Although conventional routes for the synthesis of ketones have been widely used, the potential challenge with these methods is functional group tolerance. The reported metal-free method represents a reaction with moderate functional group tolerance. The procedure is operationally convenient and shows broad substrate scope with good to excellent product yields.
Palladium nanoparticles supported on a titanium dioxide cellulose composite (PdNPs@TiO2-Cell) for ligand-free carbon-carbon cross coupling reactions
Jadhav, Sanjay,Jagdale, Ashutosh,Kamble, Santosh,Kumbhar, Arjun,Salunkhe, Rajshri
, p. 3406 - 3420 (2016/01/25)
Well-dispersed non-spherical PdNPs with a diameter of 39-45 nm supported on a TiO2-cellulose composite (PdNPs@TiO2-Cell) can be synthesized by a simple and clean route. The catalyst was well characterized by XRD, FE-SEM, EDS, and TEM techniques. The PdNPs have good dispersity on the TiO2-Cell support. This results in excellent catalytic activities for the synthesis of biphenyls, acrylates, acetylenes and prochiral ketones using low Pd loading (1 mol%) at comparatively low temperature. The effects of the nature and amount of bases, nature of solvents, amount of catalyst and the reaction temperature on the activity of PdNPs@TiO2-Cell were thoroughly investigated. The catalyst showed at least four times reusability without decrease in catalytic activity.
Ligand-free Pd catalyzed cross-coupling reactions in an aqueous hydrotropic medium
Jadhav, Sanjay N.,Kumbhar, Arjun S.,Rode, Chadrashekhar V.,Salunkhe, Rajashri S.
supporting information, p. 1898 - 1911 (2016/04/19)
A simple, efficient and ligand-free protocol for the Suzuki-Miyaura reaction and base-free Heck-Matsuda reactions under mild reaction conditions have been developed over palladium supported on activated carbon (Pd/C) in an aqueous hydrotropic solution. The catalyst Pd/C was fully characterized by TG-DTA, SEM, EDS, XRD, XPS, BET and ICP-AES analyses. This green methodology represents a cost-effective and operationally convenient method for the synthesis of a variety of biaryls, prochiral ketones, and acrylates under the conditions that are tolerant for a broad range of functional groups with good to excellent yields. The developed Pd/C-aqueous hydrotrope combined catalytic system is well suited for the 3R approach (reducible, robust, and recyclable) for different cross-coupling reactions without an appreciable loss of its activity.
Tandem nucleophilic addition-Oppenauer oxidation of aromatic aldehydes to aryl ketones with triorganoaluminium reagents
Fu, Ying,Yang, Yanshou,Hügel, Helmut M.,Du, Zhengyin,Wang, Kehu,Huang, Danfeng,Hu, Yulai
supporting information, p. 4429 - 4432 (2013/08/23)
In the presence of pinacolone, the in situ prepared triorganoaluminium reagents reacted with aromatic aldehydes to give ketones in moderate to high yield. We propose that the products are formed via a tandem organoaluminium reagents addition-Oppenauer oxidation sequence. The Royal Society of Chemistry 2013.
Gold-catalyzed reactions of enynals/enynones with norbornenes: Generation and trapping of cyclic o-quinodimethanes (o-QDMs)
Zhu, Shifa,Zhang, Zhicai,Huang, Xiaobing,Jiang, Huanfeng,Guo, Zhengjiang
supporting information, p. 4695 - 4700 (2013/05/09)
Fan-like structures: An efficient AuIII-catalyzed method to generate the highly reactive cyclic o-quinodimethane (o-QDM) species from easily available enynals or enynones is presented (see scheme). This method produced a variety of structurally unique fan-like products with the advantages of mild reaction conditions, excellent diastereoselectivities, and high functional-group tolerance. Copyright
Opioid peptidomimetics: Leads for the design of bioavailable mixed efficacy μ opioid receptor (MOR) agonist/δ opioid receptor (DOR) antagonist ligands
Mosberg, Henry I.,Yeomans, Larisa,Harland, Aubrie A.,Bender, Aaron M.,Sobczyk-Kojiro, Katarzyna,Anand, Jessica P.,Clark, Mary J.,Jutkiewicz, Emily M.,Traynor, John R.
, p. 2139 - 2149 (2013/05/08)
We have previously described opioid peptidomimetic, 1, employing a tetrahydroquinoline scaffold and modeled on a series of cyclic tetrapeptide opioid agonists. We have recently described modifications to these peptides that confer a μ opioid receptor (MOR) agonist, δ opioid receptor (DOR) antagonist profile, which has been shown to reduce the development of tolerance to the analgesic actions of MOR agonists. Several such bifunctional ligands have been reported, but none has been demonstrated to cross the blood-brain barrier. Here we describe the transfer of structural features that evoked MOR agonist/DOR antagonist behavior in the cyclic peptides to the tetrahydroquinoline scaffold and show that the resulting peptidomimetics maintain the desired pharmacological profile. Further, the 4R diastereomer of 1 was fully efficacious and approximately equipotent to morphine in the mouse warm water tail withdrawal assay following intraperitoneal administration and thus a promising lead for the development of opioid analgesics with reduced tolerance.
Copper-catalyzed arylation of arylboronic acids with aldehydes
Zheng, Hanmei,Ding, Jinchang,Chen, Jiuxi,Liu, Miaochang,Gao, Wenxia,Wu, Huayue
experimental part, p. 1626 - 1630 (2011/08/03)
A novel copper-catalyzed arylation of arylboronic acids with aldehydes under oxygen atmosphere was achieved in the presence of Cu(OTf)2 and Xantphos, affording diaryl ketone derivatives in moderate to good yields. The efficiency of this reaction was demonstrated by the compatibility with fluoro, bromo, chloro, nitro, -methylsulfonyl, and trifluoromethyl groups. Georg Thieme Verlag Stuttgart ? New York.
Simple and efficient procedure for the friedel-crafts acylation of aromatic compounds with carboxylic acids in the presence of P2O5/AL2O3 under heterogeneous conditions
Hajipour, Abdol R.,Zarei, Amin,Khazdooz, Leila,Ruoho, Arnold E.
experimental part, p. 2702 - 2722 (2009/12/06)
An efficient and chemoselective method for the Friedel-Crafts acylation of aromatic compounds using P2O5/Al2O3 and carboxylic acids. Both aromatic and aliphatic carboxylic acids reacted easily to afford the corresponding aromatic ketones in good yields.
Friedel-Crafts acylation of aromatic compounds with carboxylic acids in the presence of P2O5/SiO2 under heterogeneous conditions
Zarei, Amin,Hajipour, Abdol R.,Khazdooz, Leila
scheme or table, p. 6715 - 6719 (2009/04/07)
A convenient and efficient procedure for the Friedel-Crafts acylation of aromatic compounds with carboxylic acids in the presence of P2O5/SiO2 is described. Both aromatic and aliphatic carboxylic acids reacted easily to afford the corresponding aromatic ketones. The use of non-toxic and inexpensive materials, simple and clean work-up, short reaction times and good yields of the products are the advantages of this method.
