- Ligand-Free Iron-Catalyzed C-F Amination of Diarylamines: A One-Pot Regioselective Synthesis of Diaryl Dihydrophenazines
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A one-pot synthesis of various 5,10-diaryl-5,10-dihydrophenazines (DADHPs) from diarylamines has been achieved by using an iron-catalyzed C-F amination. Homodimerization of magnesium diarylamides, followed by defluorinative intramolecular cyclization (dou
- Aoki, Yuma,O'Brien, Harry M.,Kawasaki, Hiroto,Takaya, Hikaru,Nakamura, Masaharu
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supporting information
(2019/01/21)
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- Ligand-Free Iron-Catalyzed C-F Amination of Diarylamines: A One-Pot Regioselective Synthesis of Diaryl Dihydrophenazines
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A one-pot synthesis of various 5,10-diaryl-5,10-dihydrophenazines (DADHPs) from diarylamines has been achieved by using an iron-catalyzed C-F amination. Homodimerization of magnesium diarylamides, followed by defluorinative intramolecular cyclization (dou
- Aoki, Yuma,O'Brien, Harry M.,Kawasaki, Hiroto,Takaya, Hikaru,Nakamura, Masaharu
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supporting information
p. 461 - 464
(2019/01/23)
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- Copper-catalyzed, ceric ammonium nitrate mediated N-arylation of amines
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Cu-Catalyzed, ligand- and base-free cross-coupling of aryl boronic acids with primary and secondary amines has been reported. This ‘Chan-Evans-Lam' reaction has revealed that at room temperature, with a catalytic amount of copper(ii) acetate and ceric ammonium nitrate (CAN) as an oxidant, N-arylation can result in an effective C-N bond formation. This air stable, practical, robust protocol enables tolerance towards a variety of functional groups on both boronic acid and amine partners.
- Gonela, Uma Maheshwar,Ablordeppey, Seth Y.
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supporting information
p. 2861 - 2864
(2019/02/17)
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- Diamines as interparticle linkers for silica-titania supported PdCu bimetallic nanoparticles in Chan-Lam and Suzuki cross-coupling reactions
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A series of highly efficient amine functionalized SiO2-TiO2 supported bimetallic PdCu catalysts with varied metal composition have been synthesized. Ethane-1,2-diamine, butane-1,4-diamine and hexane-1,6-diamine were employed as interparticle linkers for amine functionalization of a SiO2-TiO2 support material so as to study the effect of pendant chain length on stabilization and immobilization of bimetallic nanoparticles. The shortest carbon chain length on the support provided the best results, which may be due to the trapping of metal nanoparticles more efficiently by the basic nitrogen sites. The catalytic activities of these materials were evaluated for C-N and C-C coupling reactions. The most active catalyst, Pd1Cu1@12DA-STS, was characterized by various techniques including SEM, HR-TEM, ICP-AES, XRD, FTIR, EDX, CHN analysis and TGA studies. Moreover, the synthesized catalyst was found to be recyclable for up to five runs without significant loss of activity.
- Jamwal, Babita,Kaur, Manpreet,Sharma, Harsha,Khajuria, Chhavi,Paul, Satya,Clark
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p. 4919 - 4928
(2019/03/26)
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- Synthesis of Di(hetero)arylamines from Nitrosoarenes and Boronic Acids: A General, Mild, and Transition-Metal-Free Coupling
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The synthesis of di(hetero)arylamines by a transition-metal-free cross-coupling between nitrosoarenes and boronic acids is reported. The procedure is experimentally simple, fast, mild, and scalable and has a wide functional group tolerance, including carbonyls, nitro, halogens, free OH and NH groups. It also permits the synthesis of sterically hindered compounds.
- Roscales, Silvia,Csák?, Aurelio G.
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supporting information
p. 1667 - 1671
(2018/03/23)
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- Copper immobilized at a covalent organic framework: An efficient and recyclable heterogeneous catalyst for the Chan-Lam coupling reaction of aryl boronic acids and amines
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A polyimide covalent organic framework (PI-COF) with high thermal and chemical stabilities has been readily prepared from commercially available and inexpensive reagents and was employed as an effective support for heterogeneous copper. It was demonstrated that the obtained Cu@PI-COF is a highly active heterogeneous catalyst which can effectively promote the Chan-Lam coupling reaction of aryl boronic acids and amines in an open flask without the aid of any base or additive. In addition, the catalyst could be readily recovered from the reaction mixture by simple filtration and reused for at least eight cycles without any observable change in structure and catalytic activity.
- Han, Yi,Zhang, Mo,Zhang, Ya-Qing,Zhang, Zhan-Hui
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p. 4891 - 4900
(2018/11/21)
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- Sulfonato-diketimine Copper(II) Complexes: Synthesis and Application as Catalysts in Chan-Evans-Lam Couplings
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Copper complexes bearing a diketimino-sulfonate ligand, LCu(NO3)(NCMe), were prepared and proved to be stable to water for several hours in solution. Prolonged standing in the presence of water or strong bases led to desulfonation of the ligand. LCu(NO3) was inactive in the polymerization of lactide (in the presence of benzyl alcohol), but showed high activity for the Chan-Evans-Lam coupling of a variety of amines and anilines. Couplings do not require addition of base, ligand, or molecular sieves. Mechanistic investigations indicate a catalytic cycle involving dioxygen as the required oxidant, precoordination of boronic acid to the sulfonate group, and transmetalation occurring prior to reaction with the nucleophile.
- Hardouin Duparc, Valérie,Schaper, Frank
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p. 3053 - 3060
(2017/09/05)
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- Highly Chemoselective Iridium Photoredox and Nickel Catalysis for the Cross-Coupling of Primary Aryl Amines with Aryl Halides
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A visible-light-promoted iridium photoredox and nickel dual-catalyzed cross-coupling procedure for the formation C?N bonds has been developed. With this method, various aryl amines were chemoselectively cross-coupled with electronically and sterically diverse aryl iodides and bromides to forge the corresponding C?N bonds, which are of high interest to the pharmaceutical industries. Aryl iodides were found to be a more efficient electrophilic coupling partner. The coupling reactions were carried out at room temperature without the rigorous exclusion of molecular oxygen, thus making this newly developed Ir-photoredox/Ni dual-catalyzed procedure very mild and operationally simple.
- Oderinde, Martins S.,Jones, Natalie H.,Juneau, Antoine,Frenette, Mathieu,Aquila, Brian,Tentarelli, Sharon,Robbins, Daniel W.,Johannes, Jeffrey W.
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supporting information
p. 13219 - 13223
(2016/10/30)
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- Solvent-free N-arylation of amines with arylboronic acids under ball milling conditions
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Solvent-free coupling reactions of arylboronic acids with various amines were presented under ball milling conditions, achieving the aromatic amine coupling products with yields ranging from moderate to good. This type of mechano-chemistry exhibited advantages of solvent-free property, high efficiency, simple work-up procedure and eco-friendliness. This journal is the Partner Organisations 2014.
- Zhu, Xingyi,Zhang, Qihong,Su, Weike
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p. 22775 - 22778
(2014/06/23)
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- Noninnocent behavior of bidentate amidophosphido [NP]2- ligands upon coordination to copper
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The synthesis and preliminary coordination chemistry of two new redox-active bidentate ligands containing amido and phosphido donors are described. Treatment of the [RNP]2- (R = Ph, 2,4,6-trimethylphenyl) ligands with CuCl2 and PMe3 results in a dimeric copper(I) P-P coupled product via ligand oxidation. The intermediate of this reaction is proposed to involve a ligand radical generated via oxidation of the [RNP]2- ligand by copper(II), and the existence of such an intermediate is probed using computational methods. Significant radical character on the phosphorus atoms of the alleged [ RNP]?-/copper(I) intermediate leads to P-P radical coupling.
- Bezpalko, Mark W.,Foxman, Bruce M.,Thomas, Christine M.
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supporting information
p. 12329 - 12331
(2013/11/19)
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- Carbazole-Containing Sulfonamides as Cryptochrome Modulators
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The subject matter herein is directed to carbazole-containing sulfonamide derivatives and pharmaceutically acceptable salts or hydrates thereof of structural formula I wherein the variable R1, R2, R3, R4, R5, R6, R7, A, B, C, D, E, F, G, H, a, and b are accordingly described. Also provided are pharmaceutical compositions comprising the compounds of formula I to treat a Cry-mediated disease or disorder, such as diabetes, obesity, metabolic syndrome, Cushing's syndrome, and glaucoma.
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Paragraph 0238-0239
(2013/11/19)
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- NOVEL ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME
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The present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device containing the same. The organic electroluminescent compounds according to the present invention have high luminescent efficiency and a lo
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Paragraph 100; 101; 102; 103; 116; 117; 118
(2014/01/07)
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- Ligand-free C-N bond formation in aqueous medium using a reusable Cu-Mn bimetallic catalyst
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A general ligand-free protocol has been described for the recyclable and reusable Cu-Mn catalyzed C-N bond forming cross coupling reaction of arylboronic acids with various amines to form N-arylated amine products in aqueous medium affording excellent yields under ambient conditions, in 3-4 h.
- Sawant, Sanghapal D.,Srinivas, Mahesuni,Aravinda Kumar,Lakshma Reddy,Singh, Parvinder Pal,Singh, Baldev,Sharma, Amit Kumar,Sharma,Vishwakarma, Ram A.
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p. 5351 - 5354
(2013/09/12)
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- Antiviral Compounds
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Novel compounds, methods, and compositions for treating various viral infections are described. In some embodiments the novel compounds of the invention are 3-oxo-phenothiazine derivatives; more specific embodiments include 3-oxo-phenothiazine derivatives having substituents at the 1-, 7-, and 9-positions of the phenothiazine parent ring. In other embodiments, the invention provides compositions and methods for treating viral infections, especially HIV.
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- Antiviral Compounds
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Compounds and methods for preventing and treating viral infections are provided. In some embodiments, novel compounds broad-spectrum antiviral activity are provided. In more specific embodiments, the compounds and methods are effective against viruses such as Venezuelan Equine Encephalitis, West Nile Virus, and Hepatitis C.
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- Highly efficient and versatile phosphine-phosphoramidite ligands for asymmetric hydrogenation
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A set of novel phosphine-phosphoramidite ligands possessing two elements of chirality have been prepared through a modular synthetic approach. The ligands (11bS)-N-[2-(diphenylphosphino)phenyl]-N-[(S)-1-phenylethyl]dinaphtho[2,1-d: 1′,2′-f][1,3,2]dioxaphosphepin-4-amine [(Sa,S c)-1a] and (11bR)-N- [2-(diphenylphosphino)phenyl]-N-[(S)-1-(1- naphthyl)ethyl]dinaphtho[2,1-d:1′,2′-f]-[1,3,2]dioxaphosphepin-4- amine [(SaSc-1b] are unique in providing enantioselectivities ≥96% ee and ≥94% ee, respectively, in mechanistically distinct hydrogenations of C=C, C=N and C=O double bonds in combination with three different transition metals (rhodium, iridium, and ruthenium, respectively). Particularly remarkable are the enantiomeric excesses up to 97% achieved in the iridium-catalyzed hydrogenation of 2-substituted quinolines, where (11b5)-N-[2-(diphenylphosphino)phenyl]-N-[(S)-1-(naphthalen-1- yl)ethyl]-8,9,10,11, 12,13,14,15-octahydrodinaphtho[2,1-i/:1′,2′-f] [1,3,2]dioxaphosphepin-4-amine [(Sa,Sc)-2] proved to be the most selective ligand. Substantially lower ees were obtained with the mismatched diastereomer (Ra,Sc)-1b and with the N-phenyl-substituted ligand 1c, missing a second element of chirality.
- Eggenstein, Matthias,Thomas, Anika,Theuerkauf, Jens,Francio, Giancarlo,Leitner, Walter
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experimental part
p. 725 - 732
(2009/12/01)
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- Emissive monomeric metal complexes
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Monomeric metal complexes having improved luminescence properties are provided. In one embodiment, a monomeric metal complex is represented by the formula [PN]M(L)2. PN is an amidophosphine ligand, and M may be any metal capable of exhibiting l
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Page/Page column 4
(2010/11/30)
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- Cu(I)-mediated reductive amination of boronic acids with nitroso aromatics.
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[reaction: see text] A mild method for the reductive amination of aryl boronic acids with nitroso aromatic compounds is reported. This C-N bond formation is mediated by a stoichiometric amount of CuCl as both a catalyst and a reducing agent. Alternatively, 10% Cu(I)-3-methylsalicylate (CuMeSal) catalyzes the same reaction in the presence of either ascorbic acid or hydroquinone as the terminal reducing agent. Diarylamines bearing a variety of functional groups can be obtained in good yields.
- Yu, Ying,Srogl, Jiri,Liebeskind, Lanny S
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p. 2631 - 2634
(2007/10/03)
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- Nickel(0)/dihydroimidazol-2-ylidene complex catalyzed coupling of aryl chlorides and amines
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A general and simple nickel-catalyzed coupling of aryl chlorides and amines is reported. The scope and limitations of the coupling process using Ni(0), 1,3-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene, and NaO-t-Bu as base were investigated. Secondary cyclic and acyclic amines and anilines provided the arylamine coupling products in good to excellent yields. Compared to palladium-catalyzed aminations, this procedure offers an alternative route to N-substituted anilines starting from readily available aryl chlorides.
- Desmarets, Christophe,Schneider, Raphael,Fort, Yves
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p. 3029 - 3036
(2007/10/03)
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- Reaction of n-aminophthalimide derivatives with aluminum chloride in benzene
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The reaction of N-aminophthalimide derivatives with AlCl3 in benzene has been investigated. From N-amino- and N-benzamidophthalimide (1a and 1b), N-amino- and N-benzamido3,3-diaryl-2,3-dihydroisoindol-1-ones (2) are obtained in high yield by initial attack of benzene on the imide carbonyl, assisted by the neighboring nitrogen atom. From N-arylaminophthalimide derivatives (4), the N-N bond is cleaved heterolytically to give an arylnitrenium ion and canonical forms involving the arene which are trapped by benzene to give aminobiaryls and N-arylanilines.
- Ohwada, Atsushi,Li, Hao,Sakamoto, Takeshi,Kikugawa, Yasuo
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p. 225 - 233
(2007/10/03)
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- Sterically Hindered N-Aryl-2(1H)-Quinolones and N-Aryl-6(5H)-Phenanthridinones: Separation of Enantiomers and Barriers to Racemization
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The novel N-aryl-4-chloro-3-methyl-2(1H)-quinolones (1)-(4) have been synthesized by condensation of the appropriate diphenylamine with diethyl methylmalonate and subsequent chlorination of the resulting N-aryl-4-hydroxy-3-methyl-2(1H)-quinolones (7)-(10). 5-(1-Naphthyl)-6(5H)-phenanthridinone (5) has been synthesized by the Chapman rearrangement of the 6-(1-naphthoxy)phenanthridine (11).Separation of the enantiomers (M) and (P) of the quinolones (1)-(4) and phenanthridinones (5), (6) was achieved by liquid chromatography on triacetylcellulose.The barriers to partial rotation about the C-N bond in (1)-(6) were determined by thermal racemization of enantiomers and are compared with those of structurally related molecules.
- Mintas, Mhaden,Mihaljevic, Vesna,Koller, Helmut,Schuster, Doris,Mannschreck, Albrecht
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p. 619 - 624
(2007/10/02)
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- THE REACTION OF ORTHO-SUBSTITUTED AROMATIC AZIDES WITH BORON TRICHLORIDE OR TRIFLUORIDE
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The reactiont of boron trichloride or trifluoride with ortho-aryl, -diazoaryl, and -arylazoaryl phenyl azides in benzene at room temperature generally gives fused azoles in high yields.Treatment of 2-nitrophenyl azide with boron trichloride mainly affords chlorinated nitroanilines, whereas with boron trifluoride it gives N-o-nitrophenylaniline.In aromatic solvents at 60 deg C in the presence of boron trifluoride-diethyl ether, 2-azidobiphenyl forms carbazole and 2-(arylamino)biphenyls, the formation of which depends greatly upon the nucleophilicity of the solvent used; however, its pseudo-first-order decomposition rate is slightly greater in benzene than in toluene or m-xylene.Under the same conditions, phenyl azide forms diarylamines.The results suggest that singlet nitrenium ions, arising from the corresponding azidetrihalogenoborane complexes by loss of molecular nitrogen, are generally the reactive intermediates.
- Spagnolo, Piero,Zanirato, Paolo
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p. 2615 - 2620
(2007/10/02)
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