- Electrochemical Synthesis of Carbazoles by Dehydrogenative Coupling Reaction
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A constant current protocol, employing undivided cells, a remarkably low supporting electrolyte concentration, inexpensive electrode materials, and a straightforward precursor synthesis enabling a novel access to N-protected carbazoles by anodic N,C bond formation using directly generated amidyl radicals is reported. Scalability of the reaction is demonstrated and an easy deblocking of the benzoyl protecting group is presented.
- Kehl, Anton,Schupp, Niclas,Breising, Valentina M.,Schollmeyer, Dieter,Waldvogel, Siegfried R.
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supporting information
p. 15847 - 15851
(2020/11/02)
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- One-pot Cascade Reaction for the Synthesis of Phenanthridines via Suzuki Coupling/C?H Oxidation/Aromatization
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A one-pot cascade coupling/annulation reaction for the synthesis of phenanthridines has been developed from arylboronic acids and o-bromo arylamides with DMSO as a carbon source. The desired phenanthridines were obtained in moderate to good yields by using simple procedure. (Figure presented.).
- Chen, Rener,Ding, Yuxin,Ma, Yongmin,Zhang, Yi
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p. 5697 - 5707
(2020/12/01)
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- Organic electroluminescent materials and devices
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The present application relates to organic electroluminescent materials and devices. The present invention discloses a compound comprising a first ligand LA selected from the group.
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- Synthesis, Isolation, and Characterization of Mono- and Bis-norbornene-Annulated Biarylamines through Pseudo-Catellani Intermediates
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A palladium-catalyzed C-H functionalization of an external ring of N-acyl 2-aminobiaryl with bicyclo[2.2.1]hept-2-ene (norbornene) via multiple C-H bond activations was developed. This study is the first report of the formation of bis-norbornene annulated biarylamines isomers (syn-3a′/anti-3a′ = 36:64) from multiple C-H bond functionalizations. Additionally, nondirected C-H bond functionalization at the C-4′ position with alkenes rendered complete C-H functionalization of five C-H bonds that formed a stable hexasubstituted benzene ring.
- Annamalai, Pratheepkumar,Hsiao, Huan-Chang,Raju, Selvam,Fu, Yi-Hsuan,Chen, Pei-Ling,Horng, Jia-Cherng,Liu, Yi-Hung,Chuang, Shih-Ching
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supporting information
p. 1182 - 1186
(2019/02/14)
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- Palladium(II)-catalyzed mono-and bis-alkenylation of N-acetyl-2-aminobiaryls through regioselective C-H bond activation
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We developed palladium-catalyzed oxidative coupling of olefins with N-acyl 2-aminobiaryls through a sequence of ortho C-H bond activation/alkene insertion/reductive elimination. Furthermore, we controlled the selectivity of mono-and bis-alkenylation products with the solvent effect. The developed protocol was promising for a broad substrate scope ranging from activated olefins with a wide variety of functional groups to unactivated olefins.
- Annamalai, Pratheepkumar,Hsu, Kou-Chi,Raju, Selvam,Hsiao, Huan-Chang,Chou, Chih-Wei,Lin, Gu-Ying,Hsieh, Cheng-Ming,Chen, Pei-Ling,Liu, Yi-Hung,Chuang, Shih-Ching
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p. 3840 - 3856
(2018/04/14)
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- Transition-metal-free and organic solvent-free conversion of N-substituted 2-aminobiaryls into corresponding carbazoles via intramolecular oxidative radical cyclization induced by peroxodisulfate
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An atom-economical and environmentally benign approach for the synthesis of N-substituted carbazoles from analogous 2-aminobiaryls using peroxodisulfate in water is reported. The reactions proceeded through an intramolecular oxidative radical cyclization
- Natarajan, Palani,Priya,Chuskit, Deachen
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supporting information
p. 5854 - 5861
(2017/12/26)
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- Palladium-Catalyzed Selective Aryl Ring C–H Activation of N-Acyl-2-aminobiaryls: Efficient Access to Multiaryl-Substituted Naphthalenes
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Palladium-catalyzed cycloaromatization of N-acyl-2-aminobiaryls, through a sequence of ortho C?H bond activation/alkyne insertion/meta C?H bond activation/alkyne insertion, was developed. An efficient synthesis of multiaryl-substituted naphthalenes, N-[2-(5,6,7,8-tetraarylnaphthalen-1-yl)aryl]acetamides, was demonstrated using molecular oxygen as the sole oxidant. Furthermore, through Buchwald's synthetic protocol, two compounds were converted into corresponding fluorescent carbazoles in 30–40% yield by intramolecular C?N bond formation. (Figure presented.).
- Annamalai, Pratheepkumar,Chen, Wu-Yin,Raju, Selvam,Hsu, Kou-Chi,Upadhyay, Nitinkumar Satyadev,Cheng, Chien-Hong,Chuang, Shih-Ching
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supporting information
p. 3642 - 3648
(2016/11/25)
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- One pot synthesis of phenanthridines using a palladium-catalyzed cyclization of aromatic ketoximes with aryl iodides: Via Beckmann rearrangement
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The catalytic reaction of ketoximes with aryl iodides via a Beckmann rearrangement in the presence of a catalytic amount of Pd(OAc)2, Ag2O and ZnBr2 gave substituted phenanthridines in good to excellent yield. In the reaction, aromatic ketoximes converted first to acetanilides in the presence of ZnBr2/TFA via a Beckmann rearrangement followed by arylation in the presence of palladium complex. Furthermore, ortho-arylated acetanilides were converted to phenanthridine derivatives in the presence of a Hendrickson reagent.
- Raju, Gajula,Guguloth, Vijayacharan,Satyanarayana, Battu
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p. 45036 - 45040
(2016/06/06)
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- Ruthenium(II)-catalyzed C-H arylation of anilides with boronic acids, borinic acids and potassium trifluoroborates
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An in situ generated cationic ruthen-ium(II) catalyst allowed for robust C-H arylations of anilides with boronic acids. The optimized ruthenium catalyst was found to be both site selective and chemoselective, thereby providing the monoarylated products in
- Hubrich, Jonathan,Himmler, Thomas,Rodefeld, Lars,Ackermann, Lutz
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supporting information
p. 474 - 480
(2015/03/05)
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- Ruthenium-catalyzed ortho-arylation of acetanilides with aromatic boronic acids: An easy route to prepare phenanthridines and carbazoles
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The highly regioselective ortho-arylation of acetanilides with aromatic boronic acids in the presence of a Ru(ii) complex (3 mol%), AgSbF6 (12 mol%), Cu(OTf)2 (20 mol%) and Ag2O (1.0 eq.) is described. Later, ortho-arylated acetanilides were converted into phenanthridine and carbazole derivatives by using Ph3PO and Tf2O or palladium or Cu(OTf)2 catalysts.
- Chinnagolla, Ravi Kiran,Jeganmohan, Masilamani
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supporting information
p. 2442 - 2444
(2014/03/21)
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- Palladium-catalysed ortho arylation of acetanilides
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The palladium-catalysed direct arylation of acetanilides by using C-H activation methodology has been demonstrated. Several acetanilides were coupled with aryl iodides in the presence of 10 mol% of Pd(OAc)2, 1.0 equiv of Cu(OTf)2, an
- Zhang, Guo-Zhen,Chen, Cheng-Qun,Feng, Xin-Hua,Huang, Guo-Sheng
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experimental part
p. 149 - 155
(2010/11/02)
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- Ortho arylation of acetanilides via Pd(II)-catalyzed C-H functionalization
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A remarkable transformation to realize ortho arylation of acetanilides via Pd(II)-catalyzed C-H functionalization with trialkoxyarylsinaes was demonstrated. Copyright
- Yang, Shangdong,Li, Bijie,Wan, Xiaobing,Shi, Zhangjie
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p. 6066 - 6067
(2008/02/02)
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- Acid-Catalyzed Reactions of N-Arylhydroxylamines and Related Compounds with Benzene. Iminium-Benzenium Ions
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N-Arylhydroxylamines react with benzene in the presence of trifluoroacetic acid (TFA) at room temperature to give diphenylamines.When TFA was replaced by a strong acid, trifluoromethanesulfonic acid (TFSA), the major products were aminobiphenyls.The nature of the reaction was explored by reactions of 4-substituted phenylhydroxylamines and dialkylaniline N-oxides with benzene.Thus, it was demonstrated that the reactive intermediates are onium-benzenium dications which are trapped by benzene to give aminobiphenyls by a mechanism similar to the Friedel-Krafts alkylation.Further evidence for the proposed reaction mechanism was the observation that nitrosobenzene and azoxybenzene reacted with benzene to give analogous products in the presence of the stronger acid.
- Shudo, Koichi,Ohta, Toshiharu,Okamoto, Toshihiko
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p. 645 - 653
(2007/10/02)
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