1173294-79-5Relevant academic research and scientific papers
Pd/Mg-La mixed oxide catalyzed oxidative sp2 CH bond acylation with alcohols
Kishore,Kantam, M. Lakshmi,Yadav,Sudhakar,Laha,Venugopal
, p. 213 - 218 (2013)
Pd/Mg-La mixed oxide is used as an efficient catalyst for the oxidative direct acylation of arene sp2 CH bonds with alcohols. TBHP was used for in situ oxidation of the alcohols to aldehydes which after coupling with 2-aryl pyridines forms aryl ketones. The catalyst is recovered and used for four cycles.
Monodisperse CuPd alloy nanoparticles as efficient and reusable catalyst for the C (sp2)–H bond activation
Huang, Fei,Wang, Feifan,Hu, Qiyan,Tang, Lin,Xu, Dongping,Fang, Yang,Zhang, Wu
, (2021/03/17)
Metal-catalyzed selective activation of C–H bonds is very important for the construction of a variety of biologically active molecules. Supported alloy nanoparticles are of great interest in various catalytic applications due to the synergistic effects between different metals. Here, well-dispersed CuPd alloy nanoparticles supported on reduced graphene oxide (rGO) were synthesized and found to be highly efficient and recyclable catalyst for the chelation-assisted C (sp2)–H bond activation. Aromatic ketones or esters were synthesized via the cross-dehydrogenative coupling (CDC) reaction between 2-arylpyridines and alcohols or acids. Moreover, the catalyst was recovered and used for five times without significantly losing activity.
Pyridine-directed carbon–carbon single bond activation: Rhodium-catalyzed decarbonylation of aryl and heteroaromatic ketones
Johnson, Jeffrey B.,Salisbury, Eric A.,Schoonover, Erik J.,VanderRoest, Jacob P.,Wagner, Cole J.
supporting information, (2021/07/28)
The decarbonylation of 2-pyridyl-substituted ketones via transition metal-catalyzed carbon–carbon bond activation provides ready access to a variety of biaryl compounds. The highly efficient and general method provides reliable decarbonylation of benzophenones including a range of functional groups and substitution patterns. The methodology has also proven highly efficient for heteroaromatic substrates, including those containing thiophenyl, indolyl, quinolinyl, and pyridine substitution.
Ruthenium-Catalyzed Carbonylative Coupling of Anilines with Organoboranes by the Cleavage of Neutral Aryl C-N Bond
Xu, Jian-Xing,Zhao, Fengqian,Yuan, Yang,Wu, Xiao-Feng
, p. 2756 - 2760 (2020/03/30)
Herein, we report the first ruthenium-catalyzed Suzuki-type carbonylative reaction of electronically neutral anilines via C(aryl)-N bond cleavage. Without any ligand and base, diaryl ketones can be obtained in moderate to high yields by using Ru3/su
Ag1Pd1-rGO nanocomposite as recyclable catalyst for CDC reactions of 2-arylpyridines with aldehydes
Hu, Qiyan,Liu, Xiaowang,Huang, Fei,Wang, Feifan,Li, Qian,Zhang, Wu
, p. 27 - 31 (2018/05/29)
Ag1Pd1 nanoparticle-reduced graphene oxide (Ag1Pd1-rGO) nanocomposite was used as an efficient catalyst for the synthesis of aromatic ketones via cross dehydrogenative coupling (CDC) reactions of 2-arylpyridines
Palladium-catalyzed decarboxylative, decarbonylative and dehydrogenative C(sp2)-H acylation at room temperature
Hossian, Asik,Manna, Manash Kumar,Manna, Kartic,Jana, Ranjan
, p. 6592 - 6603 (2017/08/16)
Over the past few decades, an impressive array of C-H activation methodology has been developed for organic synthesis. However, due to the inherent inertness of the C-H bonds (e.g. ～110 kcal mol-1 for the cleavage of C(aryl)-H bonds) harsh reaction conditions have been realized to overcome high energetic transition states resulting in a limited substrate scope and functional group tolerance. Therefore, the development of mild C-H functionalization protocols is in high demand to exploit the full potential of the C-H activation strategy in the synthesis of a complex molecular framework. Although, electron-rich substrates undergo electrophilic metalation under relatively mild conditions, electron-deficient substrates proceed through a rate-limiting C-H insertion under forcing conditions at high temperature. In addition, a stoichiometric amount of toxic silver salt is frequently used in palladium catalysis to facilitate the C-H activation process which is not acceptable from the environmental and industrial standpoint. We report herein, a Pd(ii)-catalyzed decarboxylative C-H acylation of 2-arylpyridines with α-ketocarboxylic acids under mild conditions. The present protocol does not require stoichiometric silver(i) salts as additives and proceeds smoothly at ambient temperature. A novel decarbonylative C-H acylation reaction has also been accomplished using aryl glyoxals as acyl surrogates. Finally, a practical C-H acylation via a dehydrogenative pathway has been demonstrated using commercially available benzaldehydes and aqueous hydroperoxides. We also disclose that acetonitrile solvent is optimal for the acylation reaction at room temperature and has a prominent role in the reaction outcome. Control experiments suggest that the acylation reaction via decarboxylative, decarbonylative and dehydrogenative proceeds through a radical pathway. Thus we disclose a practical protocol for the sp2 C-H acylation reaction.
Polystyrene-supported Pd(II) complex-catalysed carboacylation of 2-arylpyridines with alcohols via C─H bond activation under solvent-free conditions
Perumgani, Pullaiah C.,Parvathaneni, Sai Prathima,Keesara, Srinivas,Mandapati, Mohan Rao
, (2017/03/01)
Polystyrene-supported N,N-dimethylethylenediamine Pd(II) complex C was used as an efficient catalyst for the synthesis of aromatic ketones via ortho-acylation of sp2 C─H bonds of 2-arylpyridines with alcohols as effective coupling partners. The alcohols were oxidized with tert-butyl hydroperoxide to their corresponding aldehydes in situ and efficiently coupled with 2-arylpyridines to form aryl ketones under solvent-free conditions. Furthermore, catalyst C could be easily recovered by simple filtration and reused for five cycles without any significant decrease in its activity.
Polystyrene supported Dichloro-(8-aminoquinoline)-Palladium(II) complex catalyzed C[sbnd]H bond activation for ortho-acylation of 2-aryl pyridines
Perumgani, C. Pullaiah,Parvathaneni, Sai Prathima,Kodicherla, Balaswamy,Keesara, Srinivas,Mandapati, Mohan Rao
, p. 105 - 111 (2016/11/05)
Polystyrene-supported Dichloro-(8-aminoquinoline)-Pd(II) complex C was synthesized and its catalytic efficiency was evaluated for ortho-acylation of 2-aryl pyridines with alcohols to form aryl ketones via cross dehydrogenative coupling. In addition in the presence of Pd(II) complex, toluene derivatives were also employed as an effective coupling partner for synthesis of aromatic ketones. Furthermore, this catalyst was highly stable and could be easily recovered by simple filtration and reused for four cycles with no significant decrease in its activity and selectivity.
Palladium catalyzed ortho-C-H-acylation of 2-arylpyridines using phenylacetylenes and styrene epoxide
Zhang, Qian,Wang, Yang,Yang, Tingting,Li, Li,Li, Dong
supporting information, p. 90 - 94 (2015/12/23)
A palladium-catalyzed ortho-C-H-acylation of 2-arylpyridine using phenylacetylenes and styrene epoxide as the acylated reagents was developed. With the employment of tert-butyl hydroperoxide (TBHP) as the oxidant and a phosphorous ligand, the protocol generates corresponding aryl ketones in moderated to good yields with high regioselectivity and good functional group compatibility.
Recyclable Pd(II)complex catalyzed oxidative sp2C[sbnd]H bond acylation of 2-aryl pyridines with toluene derivatives
Perumgani, Pullaiah C.,Parvathaneni, Sai Prathima,Keesara, Srinivas,Mandapati, Mohan Rao
, p. 189 - 195 (2016/09/13)
A recyclable polymer–anchored Pd(II) complex C was synthesized and characterized using different spectroscopic techniques. In addition the catalytic efficiency of the Pd (II) complex C was evaluated for ortho-acylation of 2-aryl pyridines with toluene derivatives to form aryl ketones via cross dehydrogenative coupling. In this catalytic process toluene acts as an effective coupling partner upon sp3C[sbnd]H bond oxidation for sp2C[sbnd]H bond acylation of 2-aryl pyridines in the presence of Pd(II)/TBHP system on water. Furthermore, the catalyst C was highly stable and could be easily recovered and reused for four cycles with no significant decrease in its activity and selectivity.
