943-72-6Relevant academic research and scientific papers
Diastereodivergent [3 + 2] Annulation of Aromatic Aldimines with Alkenes via C-H Activation by Half-Sandwich Rare-Earth Catalysts
Cong, Xuefeng,Hou, Zhaomin,Mo, Zhenbo,Nishiura, Masayoshi,Zhan, Gu
supporting information, p. 5531 - 5537 (2020/04/09)
Stereodivergent catalysis is of great importance, as it can allow efficient access to all possible stereoisomers of a given product with multiple stereocenters from the same set of starting materials. We report herein the first diastereodivergent [3 + 2]
Convenient fabrication of carbon doped WO3?x ultrathin nanosheets for photocatalytic aerobic oxidation of amines
Bao, Keyan,Zhang, Shaojie,Ni, Ping,Zhang, Zixiang,Zhang, Kailong,Wang, Liangbiao,Sun, Li Xia,Mao, Wutao,Zhou, Quanfa,Qian, Yitai
, p. 311 - 317 (2018/11/23)
It is an important chemical transformation for oxidation of amines to imines, on account of very important versatile applications of imines in organic synthesis. Here, we develop a convenient way to synthesize carbon doped WO3?x ultrathin nanos
2D sp2 Carbon-Conjugated Porphyrin Covalent Organic Framework for Cooperative Photocatalysis with TEMPO
Chen, Rufan,Hao, Huimin,Lang, Xianjun,Shi, Ji-Long,Wang, Cheng
supporting information, p. 9088 - 9093 (2020/03/30)
2D covalent organic frameworks (COFs) are receiving ongoing attention in semiconductor photocatalysis. Herein, we present a photocatalytic selective chemical transformation by combining sp2 carbon-conjugated porphyrin-based covalent organic framework (Por-sp2c-COF) photocatalysis with TEMPO catalysis illuminated by 623 nm red light-emitting diodes (LEDs). Highly selective conversion of amines into imines was swiftly afforded in minutes. Specifically, the π-conjugation of porphyrin linker leads to extensive absorption of red light; the sp2 ?C=C? double bonds linkage ensures the stability of Por-sp2c-COF under high concentrations of amine. Most importantly, we found that crystalline framework of Por-sp2c-COF is pivotal for cooperative photocatalysis with (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO). This work foreshadows that the outstanding hallmarks of COFs, particularly crystallinity, could be exploited to address energy and environmental challenges by cooperative photocatalysis.
Luminescent ruffled iridium(iii) porphyrin complexes containing N-heterocyclic carbene ligands: structures, spectroscopies and potent antitumor activities under dark and light irradiation conditions
Lam, Tsz-Lung,Tong, Ka-Chung,Yang, Chen,Kwong, Wai-Lun,Guan, Xiangguo,Li, Ming-De,Kar-Yan Lo, Vanessa,Lai-Fung Chan, Sharon,Lee Phillips, David,Lok, Chun-Nam,Che, Chi-Ming
, p. 293 - 309 (2019/01/04)
A panel of iridium(iii) porphyrin complexes containing axial N-heterocyclic carbene (NHC) ligand(s) were synthesized and characterized. X-ray crystal structures of the bis-NHC complexes [IrIII(ttp)(IMe)2]+ (2a), [IrIII(oep)(BIMe)2]+ (2d), [IrIII(oep)(IiPr)2]+ (2e) and [IrIII(F20tpp)(IMe)2]+ (2f) display ruffled porphyrin rings with mesocarbon displacements of 0.483-0.594 ? and long Ir-CNHC bonds of 2.100-2.152 ?. Variable-temperature 1H NMR analysis of 2a reveals that the macrocycle porphyrin ring inversion takes place in solution with an activation barrier of 40 ± 1 kJ mol?1. The UV-vis absorption spectra of IrIII(por)-NHC complexes display split Soret bands. TD-DFT calculations and resonance Raman experiments show that the higher-energy Soret band is derived from the 1MLCT dπ(Ir) → π*(por) transition. The near-infrared phosphorescence of IrIII(por)-NHC complexes from the porphyrin-based 3(π, π*) state features broad emission bands at 701-754 nm with low emission quantum yields and short lifetimes (Φem III(por)(IMe)2]+ complexes (por = ttp and oep) are efficient photosensitizers for 1O2 generation (Φso = 0.64 and 0.88) and are catalytically active in the light-induced aerobic oxidation of secondary amines and arylboronic acid. The bis-NHC complexes exhibit potent dark cytotoxicity towards a panel of cancer cells with IC50 values at submicromolar levels. The cytotoxicity of these complexes could be further enhanced upon light irradiation with IC50 values as low as nanomolar levels in association with the light-induced generation of reactive oxygen species (ROS). Bioimaging of [IrIII(oep)(IMe)2]+ (2c) treated cells indicates that this Ir complex mainly targets the endoplasmic reticulum. [IrIII(oep)(IMe)2]+ catalyzes the photoinduced generation of singlet oxygen and triggers protein oxidation, cell cycle arrest, apoptosis and the inhibition of angiogenesis. It also causes pronounced photoinduced inhibition of tumor growth in a mouse model of human cancer.
Carbonylation Access to Phthalimides Using Self-Sufficient Directing Group and Nucleophile
Ji, Fanghua,Li, Jianxiao,Li, Xianwei,Guo, Wei,Wu, Wanqing,Jiang, Huanfeng
, p. 104 - 112 (2018/02/19)
Herein we report a novel palladium-catalyzed oxidative carbonylation reaction for the synthesis of phthalimides with high atom- and step-economy. In our strategy, the imine and H2O, which are generated in situ from the condensation of aldehyde and amine, serve as self-sufficient directing group and nucleophile, respectively. This method provides rapid access to phthalimides starting from readily available materials in a one-pot manner. Various phthalimide derivatives are constructed efficiently, including medicinally and biologically active phthalimide-containing compounds.
Structure-Reactivity Relationship in the Frustrated Lewis Pair (FLP)-Catalyzed Hydrogenation of Imines
Tussing, Sebastian,Kaupmees, Karl,Paradies, Jan
supporting information, p. 7422 - 7426 (2016/05/24)
The autoinduced, frustrated Lewis pair (FLP)-catalyzed hydrogenation of 16-benzene-ring substituted N-benzylidene-tert-butylamines with B(2,6-F2C6H3)3 and molecular hydrogen was investigated by kinetic analysis. The pKa values for imines and for the corresponding amines were determined by quantum-mechanical methods and provided a direct proportional relationship. The correlation of the two rate constants k1 (simple catalytic cycle) and k2 (autoinduced catalytic cycle) with pKa difference between imine and amine pairs (ΔpKa) or Hammett's σ parameter served as useful parameters to establish a structure-reactivity relationship for the FLP-catalyzed hydrogenation of imines.
Formal Ir-Catalyzed Ligand-Enabled Ortho and Meta Borylation of Aromatic Aldehydes via in Situ-Generated Imines
Bisht, Ranjana,Chattopadhyay, Buddhadeb
supporting information, p. 84 - 87 (2016/01/25)
The ligand-enabled development of ortho and meta C-H borylation of aromatic aldehydes is reported. It was envisaged that while ortho borylation could be achieved using tert-butylamine as the traceless protecting/directing group, meta borylation proceeds via an electrostatic interaction and a secondary interaction between the ligand of the catalyst and the substrate. These ligand-substrate electrostatic interactions and secondary B-N interactions provide an unprecedented controlling factor for meta-selective C-H activation/borylation.
Palladium-catalyzed synthesis of aldehydes from aryl halides and tert-butyl isocyanide using formate salts as hydride donors
Zhang, Ying,Jiang, Xiao,Wang, Jin-Mei,Chen, Jing-Lei,Zhu, Yong-Ming
, p. 17060 - 17063 (2015/03/30)
An efficient one-pot palladium-catalyzed hydroformylation of aryl halides to produce aromatic aldehydes has been achieved, employing tert-butyl isocyanide as a C1 resource and formate salt as a hydride donor without any additional bases. Characterized by its mild reaction conditions, easy operation and lower toxicity, this reaction can tolerate a wide array of functional groups with moderate to excellent yields.
Well-defined BiOCl colloidal ultrathin nanosheets: Synthesis, characterization, and application in photocatalytic aerobic oxidation of secondary amines
Wu, Yihui,Yuan, Bo,Li, Mingrun,Zhang, Wen-Hua,Liu, Yan,Li, Can
, p. 1873 - 1878 (2015/06/15)
We demonstrate the first colloidal synthesis of single-crystalline BiOCl ultrathin nanosheets (UTNSs) that feature a well-defined square morphology. Unlike BiOCl nanomaterials prepared by hydrothermal routes, our colloidal BiOCl UTNSs exhibit hydrophobic
Luminescent palladium(II) complexes with π-extended cyclometalated [R-C^N^N-R′] and pentafluorophenylacetylide ligands: Spectroscopic, photophysical, and photochemical properties
Chow, Pui-Keong,To, Wai-Pong,Low, Kam-Hung,Che, Chi-Ming
, p. 534 - 545 (2014/02/14)
A series of cyclometalated PdII complexes that contain π-extended R-C^N^N-R′ (R-C^N^N-R′=3-(6′-aryl-2′- pyridinyl)isoquinoline) and chloride/pentafluorophenylacetylide ligands have been synthesized and their photophysical and photochemical prop
