52095-24-6Relevant academic research and scientific papers
Rh(III)-catalyzed C-H activation reactions forming 1: H -isoindoles containing a quaternary carbon center from aryl ketones or benzylamines
Yi, Yeonhui,Lee, Hyejeong,Jun, Chul-Ho
, p. 10171 - 10174 (2016)
Rh(iii)/Cu(OAc)2 catalyzed, one-pot reactions of aryl ketones, acrylate esters and ammonium acetate or α-substituted benzylamines under microwave irradiation conditions produce 1H-isoindoles bearing a quarternary carbon center.
Single Cu(I)-Photosensitizer Enabling Combination of Energy-Transfer and Photoredox Catalysis for the Synthesis of Benzo[ b]fluorenols from 1,6-Enynes
Zheng, Limeng,Xue, Han,Zhou, Bingwei,Luo, Shu-Ping,Jin, Hongwei,Liu, Yunkui
, p. 4478 - 4482 (2021/05/26)
An efficient, mild, and atom-economical synthesis of benzo[b]fluorenols from 1,6-enynes has been developed under photocatalytic conditions. A single P/N heteroleptic Cu(I)-photosensitizer might exhibit both energy-transfer and photoredox catalytic activities in the formation of benzo[b]fluorenols.
Palladium Complexes with Phenoxy- And Amidate-Functionalized N-Heterocyclic Carbene Ligands Based on 3-Phenylimidazo[1,5- a]pyridine: Synthesis and Catalytic Application in Mizoroki-Heck Coupling Reactions with Ortho-Substituted Aryl Chlorides
Hung, Cheng-Hau,Zheng, Wei-Yuan,Lee, Hon Man
, p. 702 - 713 (2021/04/02)
Mononuclear and tetranuclear palladium complexes with functionalized "abnormal"N-heterocyclic carbene (aNHC) ligands based on 3-phenylimidazo[1,5-a]pyridine were synthesized. All of the new complexes were structurally characterized by single-crystal X-ray diffraction studies. The new complexes were applied in the Mizoroki-Heck coupling reaction of aryl chlorides with alkenes in neat n-tetrabutylammonium bromide (TBAB). The mononuclear palladium complex with a tridentate phenoxy- and amidate-functionalized aNHC ligand displayed activity superior to that of the palladium complex with a bidentate amidate-functionalized aNHC ligand. The new tetranuclear complex with the tridentate ligand displayed the best activities, capable of the activation of deactivated aryl chlorides as substrates with a low Pd atom loading. Even challenging sterically demanding ortho-substituted aryl chlorides were successfully utilized as substrates. The studies revealed that the robustness of the catalyst precursor is crucial in delivering high catalytic activities. Also, the promising use of tetranuclear palladium complexes with functionalized aNHC ligands as the catalyst precursors in the Mizoroki-Heck coupling reaction in neat TBAB was demonstrated.
Encaging palladium(0) in layered double hydroxide: A sustainable catalyst for solvent-free and ligand-free Heck reaction in a ball mill
Shi, Wei,Yu, Jingbo,Jiang, Zhijiang,Shao, Qiaoling,Su, Weike
supporting information, p. 1661 - 1668 (2017/09/27)
In this paper, the synthesis of a cheap, reusable and ligand-free Pd catalyst supported on MgAl layered double hydroxides (Pd/MgAl-LDHs) by co-precipitation and reduction methods is described. The catalyst was used in Heck reactions under highspeed ball milling (HSBM) conditions at room temperature. The effects of milling-ball size, milling-ball filling degree, reaction time, rotation speed and grinding auxiliary category, which would influence the yields of mechanochemical Heck reactions, were investigated in detail. The characterization results of XRD, ICP-MS and XPS suggest that Pd/MgAl-LDHs have excellent textural properties with zero-valence Pd on its layers. The reaction results indicate that the catalyst could be utilized in HSBM systems to afford a wide range of Heck coupling products in satisfactory yields. Furthermore, this catalyst could be easily recovered and reused for at least five times without significant loss of catalytic activity.
An efficient Pd-NHC catalyst system in situ generated from Na2PdCl4 and PEG-functionalized imidazolium salts for Mizoroki-Heck reactions in water
Sun, Nan,Chen, Meng,Jin, Liqun,Zhao, Wei,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan
supporting information, p. 1735 - 1744 (2017/09/27)
Three PEG-functionalized imidazolium salts L1-L3 were designed and prepared from commercially available materials via a simple method. Their corresponding water soluble Pd-NHC catalysts, in situ generated from the imidazolium salts L1-L3 and Na2PdCl4 in water, showed impressive catalytic activity for aqueous Mizoroki-Heck reactions. The kinetic study revealed that the Pd catalyst derived from the imidazolium salt L1, bearing a pyridine-2-methyl substituent at the N3 atom of the imidazole ring, showed the best catalytic activity. Under the optimal conditions, a wide range of substituted alkenes were achieved in good to excellent yields from various aryl bromides and alkenes with the catalyst TON of up to 10,000.
Bidentate Directing-Enabled, Traceless Heterocycle Synthesis: Cobalt-Catalyzed Access to Isoquinolines
Zhou, Shuguang,Wang, Mingyang,Wang, Lili,Chen, Kehao,Wang, Jinhu,Song, Chao,Zhu, Jin
supporting information, p. 5632 - 5635 (2016/11/17)
Traceless heterocycle synthesis based on transition-metal-catalyzed C-H functionalization is synthetically appealing but has been realized only in monodentate directing systems. Bidentate directing systems allow for the achievement of high catalytic reactivity without the need for a high-cost privileged ligand. The first bidentate directing-enabled, traceless heterocycle synthesis is demonstrated in the cobalt-catalyzed synthesis of isoquinolines via 2-hydrazinylpyridine-directed C-H coupling/cyclization with alkynes. Convenient directing group installation through a ubiquitously present ketone group allows synthetic elaboration for complex molecules.
Manganese-Catalyzed ortho-C?H Alkenylation of Aromatic N?H Imidates with Alkynes: Versatile Access to Mono-Alkenylated Aromatic Nitriles
Yang, Xiaoxu,Jin, Xiqing,Wang, Congyang
, p. 2436 - 2442 (2016/08/16)
So far, the direct C?H alkenylation of aromatic nitriles with alkynes has not been achieved. Herein, we discribe the first manganese-catalyzed C?H alkenylation of aromatic N?H imidates to access mono-alkenylated aromatic nitriles. The reaction is accelerated by the presence of a catalytic amount of sodium pivalate. This protocol is also highlighted by the simple catalytic system, good compatibility of functional groups, and excellent mono-/dialkenylation selectivity as well as E/Z stereoselectivity. (Figure presented.).
Synthesis of substituted 2-arylindanes from e -(2-stilbenyl)methanols via lewis acid-mediated cyclization and nucleophililc transfer from trialkylsilyl reagents
Sarnpitak, Pakornwit,Trongchit, Kanokrat,Kostenko, Yulia,Sathalalai, Supaporn,Gleeson, M. Paul,Ruchirawat, Somsak,Ploypradith, Poonsakdi
, p. 8281 - 8296 (2013/09/24)
A preparative method for the synthesis of functionalized 2-arylindanes has been developed via the Lewis acid-mediated ring closure of stilbenyl methanols followed by nucleophilic transfer from trialkylsilyl reagents. The reactions gave the corresponding p
Pd-catalyzed sequential C-C bond formation and cleavage: Evidence for an unexpected generation of arylpalladium(II) species
Youn, So Won,Kim, Byung Seok,Jagdale, Arun R.
supporting information; experimental part, p. 11308 - 11311 (2012/08/28)
A Pd(II)-catalyzed reaction engaging alkenyl β-keto esters is reported that leads to the formation of 1-naphthols and an unexpected generation of arylpalladium(II) species. Interception of the in situ generated arylpalladium(II) species in a Mizoroki-Heck reaction, together with additional mechanistic studies, provided strong evidence in support of the first aromatization-driven β-carbon elimination process. A single Pd catalyst served to promote a series of both C-C bond forming and cleavage events in an unprecedented manner.
Photochemical studies on aromatic γ,δ-epoxy ketones: Efficient synthesis of benzocyclobutanones and indanones
Shao, Yutian,Yang, Chao,Gui, Weijun,Liu, Yang,Xia, Wujiong
, p. 3560 - 3562 (2012/06/04)
Irradiation of terminal aromatic γ,δ-epoxy ketones with a 450 W UV lamp led to Norrish type II cyclization/semi-pinacol rearrangement cascade reaction which formed the benzocyclobutanones containing a full-carbon quaternary center, whereas irradiation of substituted aromatic γ,δ-epoxy ketones led to the indanones through a photochemical epoxy rearrangement and 1,5-biradicals cyclization tandem reaction.
