- Dynamic Kinetic Sensitization of β-Dicarbonyl Compounds—Access to Medium-Sized Rings by De Mayo-Type Ring Expansion
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Herein, we present a photocatalyzed two-carbon ring expansion of β-dicarbonyl compounds with unactivated olefins that provides facile access to medium-sized rings. Selective sensitization of the substoichiometric enol tautomer enables reactivity of substr
- Glorius, Frank,Guldi, Dirk M.,Henkel, Christian,James, Michael J.,Mai, Lukas A.,Paulisch, Tiffany O.,Strieth-Kalthoff, Felix
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supporting information
(2021/12/27)
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- Ni-Catalyzed Dual C-H Annulation of Benzimidazoles with Alkynes for Synthesis of π-Extended Heteroarenes
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Transition metal catalyzed dual C-H activation and annulation with alkynes was an attractive protocol to construct polycyclic π-extended structures. However, most of them were dominated by noble metal catalysts. Disclosed herein was the study of base-metal Ni-catalysis for dual C-H annulation of N-aromatic imidazole, which produced a range of desired polycyclic aza-quinolines in 48-95% yields. The use of bifunctional phosphine oxide ligand proved to be critical for success.
- Qi, Shao-Long,Li, Yue,Li, Jiang-Fei,Zhang, Tao,Luan, Yu-Xin,Ye, Mengchun
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supporting information
p. 4034 - 4039
(2021/05/26)
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- Efficient NIR electrochemiluminescent dyes based on ruthenium(ii) complexes containing an N-heterocyclic carbene ligand
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Three new ruthenium(ii) complexes containing an N-heterocyclic carbene (NHC) ligand (RuNHC) have been successfully synthesized and proved to be efficient near-infrared (NIR) ECL (electrogenerated chemiluminescence) luminophores. In addition to the advanta
- Zhou, Yu-Yang,Ding, Yang-Ming,Zhao, Wei,Dong, Jian-Hua,Li, Liang-Zhi,Chen, Hong-Yuan,Xu, Jing-Juan
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supporting information
p. 1254 - 1257
(2021/02/09)
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- Chan-Lam cross-coupling reaction based on the Cu2S/TMEDA system
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A catalyst based on the readily available Cu2S/TMEDA system using a stable copper(I) source was developed for the Chan-Lam cross-coupling reaction. The capability of the catalyst was demonstrated with 1H-benzo[d]imidazol-2(3H)-one, 1H-benzo[d]imidazole, and 1H-imidazole together with electron-deficient, electron-rich, and sterically demanding boronic acids at room temperature in the presence of atmospheric oxygen to give the cross-coupling products in moderate to excellent yields. In addition, the coupling reaction of 1H-benzo[d]imidazole with several pinacol or neopentylglycol boronates indicated further potential of the catalyst. The reaction conditions tolerate the hydroxyl and bromo functional groups. The catalytic system also enables to synthesize the mono-N-substituted anilines from primary aliphatic amines. However, the two model compounds for the secondary and aromatic amines, piperidine and aniline, do not react. Two sterically demanding products with the restricted C–N bond rotation, synthesized by the N-arylation of 1H-benzo[d]imidazol-2(3H)-one with o-tolylboronic acid, enabled to confirm the atropisomers prepared by the Chan-Lam cross-coupling reaction. Furthermore, an example of one-pot Chan-Lam and Suzuki-Miyaura reaction has been reported.
- Janíková, Kate?ina,Jedinák, Luká?,Volná, Tereza,Canka?, Petr
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p. 606 - 617
(2018/01/01)
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- Green synthesis of CuO nanoflakes from copper pincer complex for effective N-arylation of benzimidazole
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Nanostructured CuO is synthesized in water using copper pincer complex as precursor without any stabilizing agent and characterized by X-ray diffraction (XRD), field emission scanning electron microscopy (FESEM), transmission electron microscopy (TEM), X-
- Jerome,Kausalya,Daniel Thangadurai,Karvembu
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- 2-halogenoimidazolium salt catalyzed aza-diels-alder reaction through halogen-bond formation
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2-Halogenoimidazolium salts are found to catalyze aza-Diels-Alder reaction of aldimines with Danishefsky diene in an efficient manner. Comparative studies and titration experiments support the formation of halogen bonding between imines and catalysts.
- Takeda, Youhei,Hisakuni, Daichi,Lin, Chun-Hsuan,Minakata, Satoshi
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supporting information
p. 318 - 321
(2015/01/30)
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- N -heterocyclic carbenes: Versatile second cyclometalated ligands for neutral iridium(III) heteroleptic complexes
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With 2-(2,4-difluorophenyl)pyridine (dfppy) as the first cyclometalated ligand and different monoanionic N-heterocyclic carbenes (NHCs) as the second cyclometalated ligands, 16 blue or greenish-blue neutral iridium(III) phosphorescent complexes, (dfppy)s
- Li, Tian-Yi,Liang, Xiao,Zhou, Liang,Wu, Chen,Zhang, Song,Liu, Xuan,Lu, Guang-Zhao,Xue, Li-Sha,Zheng, You-Xuan,Zuo, Jing-Lin
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p. 161 - 173
(2015/03/03)
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- Copper(II) hydroxide complexes of N-heterocyclic carbenes and catalytic oxidative amination of arylboronic acids
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Reactions of the imidazolium salts or their corresponding silver carbene complexes with copper powder afforded unusual copper(II) hydroxide complexes of N-heterocyclic carbenes: [Cu2(μ-OH)(L1)](PF6) 2 (2; L1 = 3,5-bis(N-picolylimidazolylidenylmethy1)pyrazolate), [Cu4(μ3-OH)2(L2)2](PF 6)4 (3; L2 = 3,5-bis(N-pyridylimidazolylidenylmethy1) pyrazolate), and [Cu4(μ3-OH)2(L3) 2](PF6)4 (4; L3 = 3,5-bis(N- pyrimidylimidazolylidenylmethy1)pyrazolate). The same reaction of 3,5-bis(N-thiophenylimidazoliumylmethy1)pyrazole yielded a dinuclear Cu(II)-NHC complex, [Cu2(L4)2] (PF6)2 (5; L4 = 3,5-bis(N-thiophenylimidazolylidenylmethy1)pyrazolate). The complexes have been fully characterized by X-ray diffraction analysis, elemental analysis, and IR and ESI-MS spectra. A catalytic study shows that complex 4 is highly active in the N-arylation reactions of imidazoles and aromatic amines with arylboronic acids in methanol at room temperature under base-free conditions.
- Liu, Bo,Liu, Bin,Zhou, Yongbo,Chen, Wanzhi
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experimental part
p. 1457 - 1464
(2010/05/01)
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- A soluble base for the copper-catalyzed imidazole N-arylations with aryl halides
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CuI-catalyzed N-arylation of imidazoles with aryl bromides has been achieved in a near-homogeneous system that utilizes tetraethylammonium carbonate as base, 8-hydroxyquinoline as ligand, and H2O as cosolvent. Preliminary results with aryl chlo
- Liu, Longbin,Frohn, Mike,Xi, Ning,Dominguez, Celia,Hungate, Randy,Reider, Paul J.
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p. 10135 - 10138
(2007/10/03)
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