- [Ru(TPP)CO]-catalysed intramolecular benzylic C-H bond amination, affording phenanthridine and dihydrophenanthridine derivatives
-
Shedding light on azides: [Ru(TPP)CO] (TPP=tetraphenyl porphyrin dianion), white light and O2 were found to be a suitable catalyst combination to perform the annulation of several biaryl azides (see scheme). The high chemoselectivity of the process allows the synthesis of phenanthridines and dihydrophenanthridines in good yield and purity. Copyright
- Intrieri, Daniela,Mariani, Matteo,Caselli, Alessandro,Ragaini, Fabio,Gallo, Emma
-
p. 10487 - 10490,4
(2012)
-
Read Online
- Broad activity of diphenyleneiodonium analogues against Mycobacterium tuberculosis, malaria parasites and bacterial pathogens
-
In this study, a structure-activity relationship (SAR) compound series based on the NDH-2 inhibitor diphenyleneiodonium (DPI) was synthesised. Compounds were evaluated primarily for in vitro efficacy against Gram-positive and Gram-negative bacteria, commonly responsible for nosocomial and community acquired infections. In addition, we also assessed the activity of these compounds against Mycobacterium tuberculosis (Tuberculosis) and Plasmodium spp. (Malaria). This led to the discovery of highly potent compounds active against bacterial pathogens and malaria parasites in the low nanomolar range, several of which were significantly less toxic to mammalian cells.
- Nguyen, Nghi,Wilson, Danny W.,Nagalingam, Gayathri,Triccas, James A.,Schneider, Elena K.,Li, Jian,Velkov, Tony,Baell, Jonathan
-
-
Read Online
- Synthesis of Triphenylenes Starting from 2-Iodobiphenyls and Iodobenzenes via Palladium-Catalyzed Dual C-H Activation and Double C-C Bond Formation
-
A novel and facile approach for the synthesis of triphenylenes has been developed via palladium-catalyzed coupling of 2-iodobiphenyls and iodobenzenes. The reaction involves dual palladium-catalyzed C-H activations and double palladium-catalyzed C-C bond formations. A range of unsymmetrically functionalized triphenylenes can be synthesized with the reaction. The approach features readily available starting materials, high atom- and step-economy, and access to various unsymmetrically functionalized triphenylenes.
- Zhang, Yanghui,Pan, Shulei,Jiang, Hang,Zhang, Yu,Chen, Dushen
-
-
Read Online
- Silver ion promoted, PdII-catalyzed arylation of arenes with a free amine as directing group in aqueous medium
-
Palladium(II)-catalyzed arylation of arenes with aryl boronic acids and a free amine as directing group in aqueous medium has been developed. High reactivity and chemoselectivity for the formation of carbon-carbon bonds were achieved by the use of soluble
- Liang, Zunjun,Yao, Jinzhong,Wang, Kai,Li, Haoran,Zhang, Yuhong
-
-
Read Online
- An extremely active and general catalyst for Suzuki coupling reaction of unreactive aryl chlorides
-
β-Diketiminatophosphane Pd complex 2a acted as a powerful catalyst which allows easy access to the Suzuki coupling reaction of less reactive aryl chlorides under mild conditions. A wide range of sterically hindered and deactivated aryl chlorides could be efficiently coupled at a low catalyst loading of 0.1 mol %. Furthermore, this catalytic system also proved to be highly effective in one-pot multiple couplings.
- Lee, Dong-Hwan,Jin, Myung-Jong
-
-
Read Online
- Visible Light-Induced Radical Cyclization of Tertiary Bromides with Isonitriles to Construct Trifluoromethylated Quaternary Carbon Center
-
The reaction of trifluoromethylated tertiary bromides with isonitriles induced by visible light is reported. Defluorination was avoided in a radical process. This method provides an efficient approach to compounds containing a trifluoromethylated quaternary carbon center, most of which show excellent potential to be agrochemicals. In addition, the bromides were prepared from perfluoroisobutylene, which is a waste from industry, after several steps. This reaction shows a feasible transfer of harmful waste into useful compounds.
- Wang, Wengui,Guo, Yong,Sun, Ke,Wang, Shoufeng,Zhang, Shuxiang,Liu, Chao,Chen, Qing-Yun
-
-
Read Online
- Palladium-catalyzed interannular meta-C-H arylation
-
The interannular meta-selective C-H arylation of biaryl-2-trifluoroacetamides using Pd(ii)/norbornene catalysis is reported. The installation of a trifluoroacetyl protecting group to tune their electronic properties and binding ability is essential for in
- Ling, Peng-Xiang,Chen, Kai,Shi, Bing-Feng
-
-
Read Online
- Scalable electrochemical synthesis of diaryliodonium salts
-
Cyclic and acyclic diaryliodonium are synthesised by anodic oxidation of iodobiaryls and iodoarene/arene mixtures, respectively, in a simple undivided electrolysis cell in MeCN-HFIP-TfOH without any added electrolyte salts. This atom efficient process does not require chemical oxidants and generates no chemical waste. More than 30 cyclic and acyclic diaryliodonium salts with different substitution patterns were prepared in very good to excellent yields. The reaction was scaled-up to 10 mmol scale giving more than four grams of dibenzo[b,d]iodol-5-ium trifluoromethanesulfonate (>95%) in less than three hours. The solvent mixture of the large-scale experiment was recovered (>97%) and recycled several times without significant reduction in yield.
- Elsherbini, Mohamed,Moran, Wesley J.
-
supporting information
p. 4706 - 4711
(2021/06/11)
-
- Self-Assembled Multilayer Iron(0) Nanoparticle Catalyst for Ligand-Free Carbon-Carbon/Carbon-Nitrogen Bond-Forming Reactions
-
Self-assembled multilayer iron(0) nanoparticles (NPs, 6-10 nm), namely, sulfur-modified Au-supported Fe(0) [SAFe(0)], were developed for ligand-free one-pot carbon-carbon/carbon-nitrogen bond-forming reactions. SAFe(0) was successfully prepared using a well-established metal-nanoparticle catalyst preparative protocol by simultaneous in situ metal NP and nanospace organization (PSSO) with 1,4-bis(trimethylsilyl)-1,4-dihydropyrazine (Si-DHP) as a strong reducing agent. SAFe(0) was easy to handle in air and could be recycled with a low iron-leaching rate in reaction cycles.
- Akiyama, Toshiki,Arisawa, Mitsuhiro,Haneoka, Hitoshi,Harada, Kazuo,Hasegawa, Jun-Ya,Honma, Tetsuo,Mashima, Kazushi,Sato, Yoshihiro,Shimoda, Shuhei,Shio, Yasunori,Suzuki, Takeyuki,Tamenori, Yusuke,Tsurugi, Hayato,Tsuruta, Kazuki,Wada, Yuki,Yamada, Makito
-
supporting information
p. 7244 - 7249
(2020/10/12)
-
- Base-Free Suzuki–Miyaura Coupling Reaction Using Palladium(II) Supported Catalyst in Water
-
Abstract: The carbon–carbon bond formation via Suzuki–Miyaura reaction was performed in water as green solvent. Pd(OAc)2(PPh3)2 supported on magnesium hydroxide and cerium carbonate hydroxide composite was prepared and characterized by various techniques. The cross-coupling reaction of aryl halides carried out in water using mild conditions. The effects of temperature, solvents, the amount of catalyst and leaving groups were studied to find the optimization conditions for cross-coupling reaction. Various aryl halides were smoothly transformed into the biaryls in good yields. In addition, the catalyst also exhibited stability and catalytic performance in the cross-coupling of aryl halides. Graphical Abstract: [Figure not available: see fulltext.] A new approach is developed for carbon–carbon bond formation via Suzuki–Miyaura reaction.2 Pd(OAc)2(PPh3)2?supported on mixed magnesium hydroxide and cerium carbonate hydroxide were prepared and characterized by XRD, XPS, SEM–EDX techniques. The cross-coupling reaction of aryl halides can be carried out in water and under mild conditions (80 °C).
- Tomar, Ravi,Singh, Nidhi,Kumar, Neeraj,Tomar, Vartika,Chandra, Ramesh
-
-
- Palladium-Catalyzed Benzofulvenation of o-Arylanilines through C?H Bond Activation by Using Two Diarylacetylenes as an Implicit Benzofulvene
-
We report the first example of Pd(II)-catalyzed highly step- and atom-economical benzofulvenation through free amine-directed ortho C?H bond activation of o-arylanilines. This paper presents a novel, simple, and efficient approach for the synthesis of benzofulvene derivatives from o-arylaniline substrates through C?H bond activation with two diarylacetylenes as an implicit benzofulvene unit. The reactivity of synthesized benzofulvenes toward oxidation was investigated, and they were shown to transform into phenanthridines, oxabenzofulvenes, and fluorescent polycyclics. (Figure presented.).
- Raju, Selvam,Hsiao, Huan-Chang,Thirupathi, Selvakumar,Chen, Pei-Ling,Chuang, Shih-Ching
-
supporting information
p. 683 - 689
(2019/01/04)
-
- Metal- and additive-free cascade trifluoroethylation/cyclization of organic isoselenocyanates by phenyl(2,2,2-trifluoroethyl)iodonium triflate
-
A novel and convenient cascade trifluoroethylation/cyclization of organic isoselenocyanates by phenyl(2,2,2-trifluoroethyl)iodonium triflate is reported. A series of 2-isoselenocyanobiaryls and aryl alkyl isoselenocyanates reacted with phenyl(2,2,2-trifluoroethyl)iodonium triflate in CH2Cl2 at 40 °C under metal- and additive-free conditions for 3 h to provide the corresponding trifluoroethylselenolated phenanthridines and 3,4-dihydroisoquinoline derivatives in good to excellent yields. The reaction represents the first general approach to access trifluoroethylselenolated phenanthridines and 3,4-dihydroisoquinolines from organic isoselenocyanates.
- Zhao, Cheng-Long,Shi, Jin,Lu, Xiuqiang,Wu, Xun,Zhang, Cheng-Pan
-
supporting information
(2019/09/03)
-
- Cobalt(II)-Catalyzed [5+2] C?H Annulation of o-Arylanilines with Alkynes: An Expedient Route to Dibenzo-[b,d]azepines
-
The first example of CoCl2-catalyzed formal [5+2] oxidative annulation of o-arylanilines with alkynes was developed, giving access to various important imine-containing dibenzo-[b,d]azepine scaffolds through sequential C?C/C?N bond formation. The reaction employs catalytic amount of manganese and oxygen as cooxidants, and features a broad substrate scope. Preliminary mechanistic studies suggested that C?H activation is involved in the rate-determining step. Moreover, both internal and terminal alkynes are well tolerated in this transformation. Besides, a regioselective migratory insertion was observed when using terminal alkynes as substrates. (Figure presented.).
- Ling, Fei,Xie, Zhen,Chen, Jiachen,Ai, Chongren,Shen, Haiwei,Wang, Ze,Yi, Xiao,Zhong, Weihui
-
supporting information
p. 3094 - 3101
(2019/05/21)
-
- Cyclization of 2-Biphenylthiols to Dibenzothiophenes under PdCl2/DMSO Catalysis
-
A palladium-catalyzed synthesis of dibenzothiophenes from 2-biphenylthiols is described. This highly efficient reaction employs a simple PdCl2/DMSO catalytic system, in which PdCl2 is the sole metal catalyst and DMSO functions as an oxidant and solvent. This transformation has broad substrate scope and operational simplicity and proceeds in high yield. The synthetic utility was demonstrated by the facile synthesis of helical dinapthothiophene 3 and an eminent organic semiconductor DBTDT 4. Importantly, highly strained trithiasumanene 5, a buckybowl of considerable synthetic challenge, was observed under this catalytic system.
- Zhang, Tao,Deng, Guigang,Li, Hanjie,Liu, Bingxin,Tan, Qitao,Xu, Bin
-
p. 5439 - 5443
(2018/09/13)
-
- Nitrogen-Iodine Exchange of Diaryliodonium Salts: Access to Acridine and Carbazole
-
A nitrogen-iodine exchange protocol of diaryliodonium salts with sodium azide salt is developed for general construction of significant functional acridines and carbazoles, in which introduction of nitrogen at a late stage was successfully established avoiding heteroatom incompatibility. Inorganic sodium azide served as the sole nitrogen atom source in this transformation. The diversiform functional acridines and carbazoles were comprehensively achieved through annulated diaryliodonium salts, respectively. Notably, Acridine orange (a fluorescent indicator for cell lysosomal dye) and Carprofen (a nonsteroidal anti-inflammatory drug) were efficiently established through this protocol.
- Wang, Ming,Fan, Qiaoling,Jiang, Xuefeng
-
supporting information
p. 216 - 219
(2018/01/17)
-
- Metal-Oxidant-Free Cobalt-Catalyzed C(sp2)-H Carbonylation of ortho-Arylanilines: An Approach toward Free (NH)-Phenanthridinones
-
A traceless directing group assisted Co-catalyzed C(sp2)-H carbonylation of ortho-arylanilines for the synthesis of free (NH)-phenanthridinones in metal-based-oxidant-free fashion was accomplished. This protocol employs diisopropyl azodicarboxylate as the CO source and oxygen as the sole oxidant, and provides good yields with various functional tolerance. The methodology has been applied for the total synthesis of PARP inhibitor PJ-34. Furthermore, the kinetic isotopic effect experiments reveal the C-H bond cleavage probably occurred in the rate-determining step.
- Ling, Fei,Zhang, Chaowei,Ai, Chongren,Lv, Yaping,Zhong, Weihui
-
p. 5698 - 5706
(2018/05/23)
-
- Palladium/Norbornene Chemistry: Synthesis of Norbornene-Containing Arylsilanes Involving Double C-Si Bond Formation
-
A novel palladium-catalyzed three-component cascade reaction of aryl halides with norbornene and hexamethyldisilane has been described, which allows the simultaneous construction of two C-Si bonds and one C-C bond. The method achieves ortho C-H functionalization of aryl halides through the formation of the five-membered palladacycle, leading to norbornene-containing arylsilanes.
- Xu, Yankun,Liu, Xiaodong,Chen, Wenqi,Deng, Guobo,Liang, Yun,Yang, Yuan
-
p. 13930 - 13939
(2018/11/30)
-
- Pd/Cu-Catalyzed aerobic oxidative aromatic C-H bond activation/N-dealkylative carbonylation towards the synthesis of phenanthridinones
-
It is important to achieve diverse functionalization of tertiary anilines due to their importance in biological molecules, pharmaceutical, functional materials, and ligands. A straightforward Pd/Cu-catalyzed oxidative C-H bond activation/N-dealkylative carbonylation of tertiary [1,1′-biphenyl]-2-anilines towards the synthesis of various biologically important phenanthridin-6(5H)-ones has been developed. A wide range of functional groups are well tolerated in this transformation. Moreover, O2 is utilized as the terminal oxidant to promote the oxidative carbonylation process.
- Shi, Renyi,Niu, Huiying,Lu, Lijun,Lei, Aiwen
-
p. 1908 - 1911
(2017/02/10)
-
- Photochemical intramolecular amination for the synthesis of heterocycles
-
Polycyclic heterocycles can be formed in good to excellent yields via photochemical conversion of the corresponding substituted aryl azides under irradiation with purple LEDs in a continuous flow reactor. The experimental set-up is tolerant to UV-sensitive functional groups while affording diverse carbazoles, as well as an indole and pyrrole framework, in short reaction times. The photochemical method is presumed to progress through a mechanism differing from the other methods of azide activation involving transition metal catalysis.
- Parisien-Collette, Shawn,Cruché, Corentin,Abel-Snape, Xavier,Collins, Shawn K.
-
supporting information
p. 4798 - 4803
(2017/10/23)
-
- Synthesis of the Carbazole Scaffold Directly from 2-Aminobiphenyl by Means of Tandem C–H Activation and C–N Bond Formation
-
An efficient method for the synthesis of the carbazole scaffold was designed and investigated. The method was developed to produce substituted carbazoles by an intramolecular combination of a free amine group and an arene. The steps of the method involved tandem Pd-catalyzed C–H activation and intramolecular C–N bond formation. The method showed good functional group tolerance, and substituent(s) could be on either of the two rings or on both of the two rings of the 2-aminobiphenyl substrate. After ring closure, the reduced Pd catalyst was oxidized to PdIIby hydrogen peroxide. The novel method was also demonstrated to operate excellently with the corresponding 2-N-acetylaminobiphenyls.
- Bj?rsvik, Hans-René,Elumalai, Vijayaragavan
-
supporting information
p. 5474 - 5479
(2016/11/25)
-
- Organic electroluminescent materials and devices
-
Compounds comprising phosphorescent metal complexes comprising cyclometallated imidazo[1,2-f]phenanthridine and diimidazo[1,2-a:1′,2′-c]quinazoline ligands, or isoelectronic or benzannulated analogs thereof, are described. Organic light emitting diode devices comprising these compounds are also described.
- -
-
Page/Page column 105; 106
(2016/04/20)
-
- METAL COMPLEXES OF CYCLOMETALLATED IMIDAZO[1,2-f]PHENANTHRIDINE AND DIIMIDAZO[1,2-A:1',2'-C]QUINAZOLINE LIGANDS AND ISOELECTRONIC AND BENZANNULATED ANALOGS THEREOF
-
The present invention refers to-imidazo [1,2-f] the dee trillion which gets torn phenylphenanthridines and [1,2-a:1 ', 2' -c] quinazoline ligands, or its isoelectronic characteristic and or phosphor including analogue relates to compounds including metal complex. Furthermore, the present invention refers to these compounds including relates organic light emitting diode devices. (by machine translation)
- -
-
Paragraph 0354; 0355; 0356; 0357; 0358
(2016/10/07)
-
- MeOTf- and TBD-Mediated Carbonylation of ortho-Arylanilines with CO2 Leading to Phenanthridinones
-
Carbonylation of o-arylanilines utilizing CO2 as a carbonyl source for the synthesis of important phenanthridinones with a free (NH)-lactam motif has been described under metal-free condition. A range of o-arylanilines were transformed to the corresponding phenanthridinones in high yields.
- Wang, Sheng,Shao, Peng,Du, Gaixia,Xi, Chanjuan
-
p. 6672 - 6676
(2016/08/16)
-
- Synthesis of Fluorenes Starting from 2-Iodobiphenyls and CH2Br2 through Palladium-Catalyzed Dual C-C Bond Formation
-
A facile and efficient approach is developed for the synthesis of fluorene and its derivatives starting from 2-iodobiphenyls and CH2Br2. A range of fluorene derivatives can be synthesized under relatively mild conditions. The reaction proceeds via a tandem palladium-catalyzed dual C-C bond formation sequence through the key dibenzopalladacyclopentadiene intermediates, which are obtained from 2-iodobiphenyls through palladium-catalyzed C-H activation.
- Shi, Guangfa,Chen, Dushen,Jiang, Hang,Zhang, Yu,Zhang, Yanghui
-
supporting information
p. 2958 - 2961
(2016/07/06)
-
- Unified Protocol for Cobalt-Catalyzed Oxidative Assembly of Two Aryl Metal Reagents Using Oxygen as an Oxidant
-
The first cobalt-catalyzed oxidative cross-coupling reaction of two aryl metal reagents is described. An equivalent amount of two aryl Grignard or lithium reagents, after mediation by an equivalent amount of simple ClTi(OEt)3, was facilely assembled under the catalysis of 1 mol % of CoCl2/10 mol % of DMPU using oxygen. The cross-couplings between various aryl metal reagents, especially between two structurally similar aryl Grignard reagents, proceeded smoothly and selectively and, thus, provided a highly general and efficient method for the construction of biaryl compounds.
- Liao, Lian-Yan,Liu, Kun-Ming,Duan, Xin-Fang
-
p. 9856 - 9867
(2015/11/03)
-
- Preparation of Substituted Phenanthridines from the Coupling of Aryldiazonium Salts with Nitriles: A Metal Free Approach
-
A transition metal free approach for the synthesis of substituted phenanthridines from the coupling reaction of aryldiazonium tetrafluoroborates with nitriles has been developed. This operationally simple protocol proceeds through a substitution of aryldiazonium with nitriles followed by an intramolecular arylation to provide the corresponding phenanthridines in moderate to excellent yields. (Chemical Equation Presented).
- Ramanathan, Mani,Liu, Shiuh-Tzung
-
supporting information
p. 5329 - 5336
(2015/05/27)
-
- Water-soluble salen-Pd complex as an efficient catalyst for Suzuki-Miyaura reaction of sterically hindered substrates in pure water
-
Water-soluble 2N2O-salen ligands and their palladium complexes were synthesized and used as efficient catalysts for the Suzuki-Miyaura reactions in pure water. Notably, the reactions of substrates with sterically demanding ortho substituents (aryl bromides and/or arylboronic acids) proceed smoothly to generate corresponding products with moderate to high yields using 0.5 mol % (salph)Pd (salph=N,N′-bis(4-SO3Na-salicylidene)-1,2-phenylenediamine) as the catalyst. Importantly, the catalytic system has the wide substrate scope and the high tolerance to various functional groups, including cyano, amino, nitro, methoxy, and acetyl. Moreover, the biaryl compounds were also obtained on a multi-gram scale by simple recrystallization with the system in the absence of any organic solvent, surfactant, or phase transfer agent and the catalyst was reused directly for the next cycle. Particularly, this protocol can be applied to synthesize aryl-substituted carbazolyl compounds.
- Liu, Ya-Shuai,Gu, Ning-Ning,Liu, Ping,Ma, Xiao-Wei,Liu, Yan,Xie, Jian-Wei,Dai, Bin
-
supporting information
p. 7985 - 7989
(2015/12/31)
-
- Direct synthesis of N -H carbazoles via iridium(III)-catalyzed intramolecular C-H amination
-
The iridium-catalyzed dehydrogenative cyclization of 2-aminobiphenyls proceeds smoothly in the presence of a copper cocatalyst under air as a terminal oxidant through intramolecular direct C-H amination to produce N-H carbazoles. A similar iridium/copper system can also catalyze the unprecedented dimerization reaction of 2-aminobiphenyl involving 2-fold C-H/N-H couplings.
- Suzuki, Chiharu,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
-
supporting information
p. 1597 - 1600
(2015/03/30)
-
- Synthesis of 6-(arylthio)phenanthridines by copper-catalyzed tandem reactions of 2-biaryl isothiocyanates with diaryliodonium salts
-
A novel copper-catalyzed tandem C-S/C-C bond-forming reaction of 2-biaryl isothiocyanates with diaryliodonium salts was developed. This is the first general approach to synthesize phenanthridines from 2-biaryl isothiocyanates. This methodology has been successfully applied to the synthesis of trisphaeridine.
- Guo, Weisi,Li, Shoulei,Tang, Lin,Li, Ming,Wen, Lirong,Chen, Chao
-
supporting information
p. 1232 - 1235
(2015/03/14)
-
- Synthesis of 6-acyl phenanthridines by oxidative radical decarboxylation-cyclization of α-oxocarboxylates and isocyanides
-
A silver catalysed synthesis of 6-acyl phenanthridines by oxidative radical decarboxylation-cyclization of α-oxocarboxylates and isocyanides was developed. This reaction provided a novel method to realize C1 insertion via a radical process and various functional groups were well-tolerated. The Royal Society of Chemistry.
- Liu, Jie,Fan, Chao,Yin, Hongyu,Qin, Chu,Zhang, Guoting,Zhang, Xu,Yi, Hong,Lei, Aiwen
-
supporting information
p. 2145 - 2147
(2014/02/14)
-
- Synthesis of carbazoles by copper-catalyzed intramolecular C-H/N-H coupling
-
A Cu-catalyzed intramolecular C-H amination for the synthesis of carbazoles has been developed. The key to success is the installation of the picolinamide-based directing group, which is spontaneously removed after the coupling event. The Cu catalysis proceeded smoothly under Pd- and I(III)-free conditions, and its mild oxidation aptitude enables the rapid and concise construction of heteroatom-incorporated carbazole core π-systems.
- Takamatsu, Kazutaka,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
-
supporting information
p. 2892 - 2895
(2014/06/23)
-
- NON-PEPTIDIC NEUROPEPTIDE Y RECEPTOR MODULATORS
-
The invention provides compounds that are modulators of neuropeptide Y (NPY) receptors, which can be selective inhibitors of NPY receptor Y2R. NPY receptor modulatory compounds are of the general formula Ar2-Y-Ar1-W-Ar3, wherein the variables are as defined herein. Compounds of the invention can be used for treatment of malconditions in patients wherein modulation of an NPY receptor is medically indicated, for example including drug or alcohol abuse, anxiety disorders, depression, stress-related disorders, neurological disorders, nerve degeneration, osteoporosis or bone loss, sleep/wake disorders, cardiovascular diseases, obesity, anorexia, inovulation, fertility disorders, angiogenesis, cell proliferation, learning and memory disorders, migraine and pain.
- -
-
Page/Page column 249
(2014/08/07)
-
- 6-Aroylated phenanthridines via base promoted homolytic aromatic substitution (BHAS)
-
Readily accessible 2-isocyanobiphenyls react with aromatic aldehydes via base promoted homolytic aromatic substitution (BHAS) to give 6-aroylated phenanthridines. Reactions occur via addition of acyl radicals to the isonitrile functionality and subsequent intramolecular BHAS of the intermediate imidoyl radicals. Initiation of the radical chain reaction is best achieved with small amounts of FeCl3 (0.4 mol %), and the commercially available and cheap tBuOOH is used as the oxidant.
- Leifert, Dirk,Daniliuc, Constantin Gabriel,Studer, Armido
-
supporting information
p. 6286 - 6289
(2014/01/17)
-
- Free-amine directed arylation of biaryl-2-amines with aryl iodides by palladium catalysis
-
A new palladium-catalyzed free-amine directed arylation of C(sp 2)-H bonds in the presence of AgOAc and TFA is described. Biaryl-2-amines react with various aryl iodides to give the corresponding mono- or diarylated products with exclusive regioselectivity.
- Liang, Zunjun,Feng, Ruokun,Yin, Hong,Zhang, Yuhong
-
supporting information
p. 4544 - 4547
(2013/09/24)
-
- Pd(II)-catalyzed C(sp2)-H carbonylation of biaryl-2-amine: Synthesis of phenanthridinones
-
A Pd(OAc)2-catalyzed C(sp2)-H carbonylation protocol of arenes under carbon monoxide atmosphere has been developed. The scope of the carbonylation reaction is broad and tolerates a variety of useful functional groups. This reaction provides a novel and efficient method for the synthesis of biologically and pharmaceutically significant phenanthridinones.
- Liang, Zunjun,Zhang, Jitan,Liu, Zhanxiang,Wang, Kai,Zhang, Yuhong
-
p. 6519 - 6526
(2013/07/26)
-
- PhI(OAc)2-mediated synthesis of 6-(trifluoromethyl) phenanthridines by oxidative cyclization of 2-isocyanobiphenyls with CF 3SiMe3 under metal-free conditions
-
A mild and efficient method for the synthesis of 6-(trifluoromethyl) phenanthridines through oxidative cyclization of 2-isocyanobiphenyls with CF3SiMe3 under metal-free conditions was developed. The reaction allows the direct formation of C-CF3 bonds and rapid access to phenanthridine ring systems in one catalytic cycle.
- Wang, Qile,Dong, Xichang,Xiao, Tiebo,Zhou, Lei
-
supporting information
p. 4846 - 4849
(2013/10/08)
-
- Highly chemoselective Mono-Suzuki arylation reactions on all three dichlorobenzene isomers and applications development
-
A Pd catalyst system is described that allows very high chemoselective monoarylation on all three isomers of dichlorobenzene. Direct application of these commodity chemicals to high-value ligands, anilines, azides, and carbazoles was achieved through this process discovery.
- Ullah, Ehsan,McNulty, James,Robertson, Al
-
p. 2127 - 2131
(2012/06/01)
-
- Phenanthrene synthesis by eosin Y-catalyzed, visible light- Induced [4+2] benzannulation of biaryldiazonium salts with alkynes
-
A metal-free, visible light-induced [4+2] benzannulation of biaryldiazonium salts with alkynes was developed. With eosin Y as photoredox catalyst, a variety of 9-substituted or 9,10-disubstituted phenanthrenes were obtained via a cascade radical addition and cyclization sequence. Copyright
- Xiao, Tiebo,Dong, Xichang,Tang, Yanchi,Zhou, Lei
-
supporting information
p. 3195 - 3199
(2013/01/16)
-
- Free-amine-directed alkenylation of C(sp2)-H and cycloamination by palladium catalysis
-
A new protocol for the palladium-catalyzed free-amine-directed alkenylation of C(sp2)-H bonds and cycloamination is described. Substituted biaryl-2-amines react with various alkenes, including electron-deficient alkenes, aryl alkenes and alkyl alkenes, to give the corresponding phenanthridines with exclusive regioselectivity. The use of α-branched styrenes leads to the formation of tricyclic compounds with a seven-membered amine ring. The method operates through a free-amine-directed alkenylation and a subsequent hydroamination cyclization reaction. Seven-membered cycloamination: A new protocol for the palladium-catalyzed free-amine-directed alkenylation of C(sp2)-H bonds and subsequent cycloamination is described (see scheme). Substituted biaryl-2-amines react with various alkenes to give the corresponding phenanthridines with exclusive regioselectivity. The use of α-branched styrenes leads to the formation of tricyclic compounds with a seven-membered amine ring. Copyright
- Liang, Zunjun,Ju, Long,Xie, Yongju,Huang, Lehao,Zhang, Yuhong
-
supporting information
p. 15816 - 15821
(2013/01/16)
-
- Phosphorescent condensed ring carbene metal complexes for use in organic light emitting devices
-
The invention relates to a compound comprising a phosphorescent metal complex comprising a monoanionic, bidentate ligand; wherein the metal is selected from the group consisting of the non-radioactive metals with atomic numbers greater than 40; and wherein the bidentate ligand comprises a carbene donor and may be linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand.
- -
-
-
- Imidazoline derivatives as alpha-1A adrenoceptor ligands
-
Compound of formula (I) or a pharmaceutically acceptable salt or solvate thereof are disclosed. Such compounds are useful in the treatment of Alpha-1A mediated diseases or conditions such as urinary incontinence.
- -
-
Page/Page column 28
(2010/02/11)
-
- Structure-based design of nonpeptide inhibitors of interleukin-1β converting enzyme (ICE, Caspase-1)
-
A novel class of reversible inhibitors of Interleukin-1β-converting enzyme (ICE, caspase-1) were discovered by iterative structure-based design. Guided by the X-ray crystal structure of analogues 1, 7 and 10 bound to ICE, we have designed a non-peptide series of small molecule inhibitors. These compounds incorporate an arylsulfonamide moiety which replaces Val-His unit (P3-P2 residues) amino acids of the native substrate. The synthesis of the core structure, structure-activity relationships (SARs), and proposed binding orientation based on molecular modeling studies for this serie of ICE inhibitors are described. Copyright
- Shahripour, Aurash B,Plummer, Mark S,Lunney, Elizabeth A,Albrecht, Hans P,Hays, Sheryl J,Kostlan, Catherine R,Sawyer, Tomi K,Walker, Nigel P.C,Brady, Kenneth D,Allen, Hamish J,Talanian, Robert V,Wong, Winnie W,Humblet, Christine
-
-
- N- and C-attacks on aromatics of phenylnitrenium ion generated from N-phenylhydroxylamine in the presence of trifluoroacetic acid containing polyphosphoric acid or trifluoroacetic anhydride
-
A phenylnitrenium ion formed from N-phenylhydroxylamine in the presence of trifluoroacetic acid (TFA) containing polyphosphoric acid (PPA) interacts with the counterion -O2CCF3 and the unshared electron-pair of H2O, showing Hammett's ρ values -5.2 and -4.0 for N- and C-attacks on aromatics PhX (X = H, Me, Et, Ph and Cl), respectively. The ratio N-/C-attack for this nitrenium ion is lower than for the nitrenium ion interacting with only the counterion; the latter nitrenium ion is generated by the use of trifluoroacetic anhydride (TFAA) instead of PPA or by reaction of phenyl azide with aromatics in TFA. The ratio for the former nitrenium ion is affected by the aromatic substituent X:X = Me > X = Et > X = Ph > X = H > X = OMe at 20 and 50°C. The order for X = Cl is between those of X = H and X = Ph at 20°C, but highest at 50°C. The ratio is increased by higher reaction temperature and by decreased concentration of TFA. The results are demonstrated from the mechanistic viewpoint for the nitrenium ions.
- Takeuchi, Hiroshi,Taniguchi, Tomohito,Ueda, Takahiro
-
p. 295 - 300
(2007/10/03)
-
- THE REACTION OF 1-ARYL-3-ALKYLTRIAZENES WITH POSITIVE HALOGENE COMPOUNDS
-
The title reaction forming arylnitrenes is described; these intermediates react in triplet state only.
- Orazi, Orfeo O.,Corral, Reneee A.,Zinczuk, Juan,Schuttenberg, Herman
-
p. 293 - 294
(2007/10/02)
-
- Acid-Catalyzed Reactions of N-Arylhydroxylamines and Related Compounds with Benzene. Iminium-Benzenium Ions
-
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
-
p. 645 - 653
(2007/10/02)
-
