- Photoredox catalysis using infrared light via triplet fusion upconversion
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Recent advances in photoredox catalysis have made it possible to achieve various challenging synthetic transformations, polymerizations and surface modifications1–3. All of these reactions require ultraviolet- or visible-light stimuli; however,
- Ravetz, Benjamin D.,Pun, Andrew B.,Churchill, Emily M.,Congreve, Daniel N.,Rovis, Tomislav,Campos, Luis M.
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Read Online
- Catalyst-free synthesis of phenanthridinesviaelectrochemical coupling of 2-isocyanobiphenyls and amines
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Catalyst free synthesis of 6-aryl phenanthridines and amides through an electrochemical reaction is reported in this study. The coupling reaction proceeds by the cathodic reduction ofin situformed diazonium ions, which are formed from anilines and an alkyl nitrite. The generated aryl radical diazonium ions coupled from isocyanides furnished the desired products in good yields. This cascade reaction was conducted in an undivided cell equipped with an RVC as the anode and Pt as the cathode usingnBu4NBF4as the electrolyte at room temperature. A series of detailed mechanistic studies have also been performed, including a radical clock experiment and cyclic voltammetry analysis.
- Malviya, Bhanwar Kumar,Singh, Karandeep,Jaiswal, Pradeep K.,Karnatak, Manvika,Verma, Ved Prakash,Badsara, Satpal Singh,Sharma, Siddharth
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p. 6367 - 6378
(2021/04/16)
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- Modular Access to Spiro-dihydroquinolines via Scandium-Catalyzed Dearomative Annulation of Quinolines with Alkynes
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The catalytic enantioselective construction of three-dimensional molecular architectures from planar aromatics such as quinolines is of great interest and importance from the viewpoint of both organic synthesis and drug discovery, but there still exist many challenges. Here, we report the scandium-catalyzed asymmetric dearomative spiro-annulation of quinolines with alkynes. This protocol offers an efficient and selective route for the synthesis of spiro-dihydroquinoline derivatives containing a quaternary carbon stereocenter with an unprotected N-H group from readily accessible quinolines and diverse alkynes, featuring high yields, high enantioselectivity, 100% atom-efficiency, and broad substrate scope. Experimental and density functional theory studies revealed that the reaction proceeded through the C-H activation of the 2-aryl substituent in a quinoline substrate by a scandium alkyl (or amido) species followed by alkyne insertion into the Sc-aryl bond and the subsequent dearomative 1,2-addition of the resulting scandium alkenyl species to the C=N unit in the quinoline moiety. This work opens a new avenue for the dearomatization of quinolines, leading to efficient and selective construction of spiro molecular architectures that were previously difficult to access by other means.
- Lou, Shao-Jie,Luo, Gen,Yamaguchi, Shigeru,An, Kun,Nishiura, Masayoshi,Hou, Zhaomin
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supporting information
p. 20462 - 20471
(2021/12/03)
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- Method for rapidly synthesizing phenanthridine compounds
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The invention discloses a method for rapidly synthesizing phenanthridine compounds. The method comprises the following steps of: uniformly mixing 9-fluorenol 1 serving as a starting raw material and azide 2 in a solvent at room temperature, slowly dropwis
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Paragraph 0015-0016; 0045-0049
(2021/08/19)
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- Ring-Expansion Strategy for α-Aryl Azahelicene Construction: Building Blocks for Optoelectronic Materials
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An acid-mediated rapid synthesis of α-aryl azahelicenes via C-C bond cleavage of helical 9H-fluoren-9-ols is reported. The newly introduced aryl ring and pyridine moieties provide an excellent opportunity to further tune the properties of azahelicences: i.e., photoluminescence. The novel α-aryl azahelicenes showcase high circularly polarized luminescence (CPL) efficiencies (4.5 × 10-3) as well as CPL brightness (BCPL), reaching 7.39 M-1 cm-1, which indicates a potential application as chiral emitters.
- Chao, Zengyin,Feng, Jia,Gu, Zhenhua,Hong, Biqiong,Wang, Limin,Xue, Xiaoping
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supporting information
p. 8056 - 8061
(2021/10/25)
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- Construction of 2-Amino-2′-ketonyl Biaryls via Acid-Mediated Ring Opening of 9 H-Fluoren-9-ols with Organic Azides
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A direct cross-coupling between 9H-fluoren-9-ols and organic azides for the synthesis of steric hindered 2-amino-2′-ketonyl biaryls was reported. The reaction featured an acid-mediated azidation/ring-expansion/hydrolysis cascade, which formally realized t
- Yang, Shan,Hong, Biqiong,Feng, Jia,Gu, Zhenhua
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supporting information
p. 9179 - 9183
(2021/11/30)
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- Synthesis of phenanthridines by I2-mediated sp3C-H amination
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An I2-mediated synthesis of phenanthridinesviaintramolecular sp3C-H amination of readily accessible aniline precursors is reported. The present synthetic process is straightforward and applicable to a broad variety of unprotected ani
- Chang, Junbiao,Fang, Benyao,Hou, Jiao,Tian, Jinyue,Yu, Wenquan
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p. 3312 - 3323
(2020/05/14)
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- Synthesis of phenanthridines through iodine-supported intramolecular C-H amination and oxidation under visible light
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Herein, we report a metal-free and step-economic synthesis of phenanthridines from 2-biarylmethanamines under mild conditions. The reaction involves iodine-supported intramolecular C-H amination and oxidation of 5,6-dihydrophenanthridine under air and benign visible light. The mechanism study reveals that visible light plays a key role in both these steps.
- Chen, Xuenian,Ma, Yan-Na,Gao, Yan,Jing, Yi,Li, Lixin,Zhang, Jie
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p. 12187 - 12198
(2020/11/10)
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- Preparation of phenanthridines from N-(o-arylbenzyl)trifluoromethanesulfonamides with 1,3-diiodo-5,5-dimethylhydantoin
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Treatment of N-(o-arylbenzyl)trifluoromethanesulfonamides with 1,3-diiodo-5,5-dimethylhydantoin in 1,2-dichloroethane under irradiation with a tungsten lamp, followed by the reaction with tBuOK gave the corresponding 6-arylphenanthridines and 6-unsubstituted phenanthridines in good to moderate yields, respectively. The reaction proceeds through an oxidative cyclization onto the aromatic ring by sulfonamidyl radicals formed from the N-iodosulfonamides. The present reaction is a one-pot method for the preparation of both 6-arylphenanthridines and 6-unsubstituted phenanthridines from N-(o-arylbenzyl)trifluoromethanesulfonamides under transition-metal-free conditions.
- Yanai, Kei,Togo, Hideo
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- TRIPLET FUSION UPCONVERSION FOR INFRARED-SENSITIZED PHOTOREDOX CHEMISTRY
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Various exemplary photoreactions can be provided, including reactions generally based on triplet-triplet annihilation upconversion. Representative photosensitizers include PdPc(OBu)8 and PtTPTNP. Representative annihilators include FDPP and TTBP. Such exe
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Paragraph 0125; 0138
(2019/09/20)
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- Rhodium(I)-Catalyzed Aryl C-H Carboxylation of 2-Arylanilines with CO2
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An unprecedented Rh(I)-catalyzed, amino-group-assisted C-H carboxylation of 2-arylanilines with CO2 under redox-neutral conditions has been developed. This reaction was promoted by a phosphine ligand with t-BuOK as the base and did not require the use of additional strong organometallic reagent. It enabled an efficient direct conversion of a broad range of 2-(hetero)arylanilines including electron-deficient heteroarenes to various phenanthridinones. Possible intermediates of the reaction were also evaluated in the preliminary mechanistic studies.
- Gao, Yuzhen,Cai, Zhihua,Li, Shangda,Li, Gang
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p. 3663 - 3669
(2019/05/17)
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- MANUFACTURING METHOD OF PHENANTHRIDINE COMPOUND
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PROBLEM TO BE SOLVED: To provide a manufacturing method of a phenanthridine compound enhancing manufacturing easiness and reducing manufacturing cost. SOLUTION: There is provided a manufacturing method for mixing an imine compound of the following formula and an iodination agent. R1 is an aliphatic group or an aromatic group, R2 to R9 are H, a halogen atom, a linear or branched alkyl group with 1 to 12 carbon atoms, which may be substituted, an aromatic group which may be substituted, or the like, and may form aromatic or non-aromatic ring by binding each other. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT
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Paragraph 0046; 0047
(2020/01/23)
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- Base-Promoted Aerobic Oxidation/Homolytic Aromatic Substitution Cascade toward the Synthesis of Phenanthridines
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The current protocol represents a transition metal-free synthesis of polysubstituted phenanthridines from abundant starting materials like benzhydrol and 2-iodoaniline derivatives. The reaction involves sequential oxidation of alcohol and direct condensation reaction with the amine resulting in a C?N bond formation followed by a radical C?C coupling in a cascade sequence. The used base potassium tert-butoxide plays a dual role in dehydrogenation and homolytic aromatic substitution reaction. Using this methodology, twenty substituted phenanthridine derivatives were synthesized with up to 85% isolated yield. (Figure presented.).
- Maiti, Debabrata,Halder, Atreyee,De Sarkar, Suman
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supporting information
p. 4941 - 4948
(2019/11/03)
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- Visible-Light-Photosensitized Aryl and Alkyl Decarboxylative Functionalization Reactions
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Despite significant progress in aliphatic decarboxylation, an efficient and general protocol for radical aromatic decarboxylation has lagged far behind. Herein, we describe a general strategy for rapid access to both aryl and alkyl radicals by photosensitized decarboxylation of the corresponding carboxylic acids esters followed by their successive use in divergent carbon–heteroatom and carbon–carbon bond-forming reactions. Identification of a suitable activator for carboxylic acids is the key to bypass a competing single-electron-transfer mechanism and “switch on” an energy-transfer-mediated homolysis of unsymmetrical σ-bonds for a concerted fragmentation/decarboxylation process.
- Patra, Tuhin,Mukherjee, Satobhisha,Ma, Jiajia,Strieth-Kalthoff, Felix,Glorius, Frank
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supporting information
p. 10514 - 10520
(2019/07/12)
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- Palladium-Catalyzed Benzofulvenation of o-Arylanilines through C?H Bond Activation by Using Two Diarylacetylenes as an Implicit Benzofulvene
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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
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supporting information
p. 683 - 689
(2019/01/04)
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- Introduction of Heteroaromatic Bases onto Cycloalkanes with BPO
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Heteroaromatic bases, such as lepidine, phenanthridine, isoquinoline, etc., were treated with cycloalkanes, such as cyclopentane, cyclohexane, cycloheptane, cyclooctane, etc., under warming conditions with benzoyl peroxide (BPO) to form heteroaromatic bases bearing cycloalkyl groups in good yields. Here, the inert C(sp3)-H bond of cycloalkanes could be functionalized to C(sp3)-heteroaromatic bases via an oxidative radical reaction pathway under transition-metal-free conditions.
- Zhou, Luan,Togo, Hideo
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p. 1627 - 1634
(2019/02/19)
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- 6-Arylphenanthridines from Aryl o-Biaryl Ketones with 1,1,1,3,3,3-Hexamethyldisilazane and Molecular Iodine
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Warming treatment of aryl o-biaryl ketones with 1,1,1,3,3,3-hexamethyldisilazane in the presence of Sc(OTf)3 in toluene, followed by the reaction with molecular iodine and K2CO3 in a mixture of THF and methanol at 60 °C gave the corresponding 6-arylphenanthridines in good to moderate yields. The present reaction is a one-pot method for the preparation of 6-arylphenanthridines from aryl o-biaryl ketones through the cyclization of imino-nitrogen-centered radicals that were generated from N-iodo aryl o-biaryl ketimines formed from the reaction of aryl biaryl ketimines with molecular iodine.
- Kobayashi, Eiji,Kishi, Atsushi,Togo, Hideo
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p. 7335 - 7347
(2019/11/22)
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- Preparation of Phenanthridines from o-Cyanobiaryls via Addition of Organic Lithiums to Nitriles and Imino Radical Cyclization with Iodine
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Simple treatment of 2-cyanobiaryls with methyllithium, ethylmagnesium bromide, butyllithium, phenyllithium, p-methylphenyllithium, etc., followed by the reaction with water and then with molecular iodine at 60 °C provided efficiently 6-methyl-, 6-ethyl-, 6-butyl-, 6-phenyl, 6-(p-methylphenyl)phenanthridines, etc., in good yields, respectively. Here, imines formed through the addition of carbanion onto the nitriles reacted with molecular iodine to form N-iodoimines smoothly, and their warming treatment induced the formation of imino radicals that smoothly cyclized onto the aryl group to give 6-alkyl- and 6-arylphenanthridines.
- Kishi, Atsushi,Moriyama, Katsuhiko,Togo, Hideo
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p. 11080 - 11088
(2018/09/12)
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- Rapid synthesis of polysubstituted phenanthridines from simple aliphatic/aromatic nitriles and iodo arenes: Via Pd(ii) catalyzed domino C-C/C-C/C-N bond formation
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An efficient and straightforward method has been developed for the synthesis of polysubstituted phenanthridines from simple aryl iodides and alkyl/aryl nitriles via the palladium-catalyzed nucleophilic addition of aryl iodides to nitriles followed by casc
- Jaiswal, Yogesh,Kumar, Yogesh,Pal, Jagannath,Subramanian, Ranga,Kumar, Amit
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supporting information
p. 7207 - 7210
(2018/07/03)
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- Synthesis method of 6-phenylphenanthridine compound
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The invention discloses a synthesis method of a 6-phenylphenanthridine compound. The synthesis method comprises the following steps of using a benzoic acid compound and 2-isocyanobiphenyl as reactionraw materials, adding a catalyst, a ligand, an oxidant a
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Paragraph 0038-0045
(2018/08/03)
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- Coupling N-H Deprotonation, C-H Activation, and Oxidation: Metal-Free C(sp3)-H Aminations with Unprotected Anilines
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An intramolecular oxidative C(sp3)-H amination from unprotected anilines and C(sp3)-H bonds readily occurs under mild conditions using t-BuOK, molecular oxygen and N,N-dimethylformamide (DMF). Success of this process, which requires mildly acidic N-H bonds and an activated C(sp3)-H bond (BDE 85 kcal/mol), stems from synergy between basic, radical, and oxidizing species working together to promote a coordinated sequence of deprotonation: H atom transfer and oxidation that forges a new C-N bond. This process is applicable for the synthesis of a wide variety of N-heterocycles, ranging from small molecules to extended aromatics without the need for transition metals or strong oxidants. Computational results reveal the mechanistic details and energy landscape for the sequence of individual steps that comprise this reaction cascade. The importance of base in this process stems from the much greater acidity of transition state and product for the 2c,3e C-N bond formation relative to the reactant. In this scenario, selective deprotonation provides the driving force for the process.
- Evoniuk, Christopher J.,Gomes, Gabriel Dos Passos,Hill, Sean P.,Fujita, Satoshi,Hanson, Kenneth,Alabugin, Igor V.
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p. 16210 - 16221
(2017/11/22)
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- Metal-free photocatalyzed cross coupling of aryl (heteroaryl) bromides with isonitriles
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A visible-light-catalyzed synthesis of 6-aryl substituted phenanthridines from aryl bromides and 2-isocyanobiphenyls at room temperature has been discovered. This metal-free cross-coupling reaction offers rapid and sustainable access to a series of struct
- Li, Xiangguang,Liang, Deqiang,Huang, Wenzhong,Sun, Huanli,Wang, Lvsu,Ren, Mengran,Wang, Baoling,Ma, Yinhai
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p. 7094 - 7099
(2017/11/13)
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- Reagent-Free C?H/N?H Cross-Coupling: Regioselective Synthesis of N-Heteroaromatics from Biaryl Aldehydes and NH3
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An unprecedented synthesis of N-heteroaromatics from biaryl aldehydes and NH3 through reagent-free C?H/N?H cross-coupling has been developed. The electrosynthesis uses NH3 as an inexpensive and atom-economic nitrogen donor, requires no oxidizing agents, and allows efficient and regioselective access to a wide range of phenanthridines and structurally related polycyclic N-heteroaromatic products.
- Zhao, Huai-Bo,Liu, Zhan-Jiang,Song, Jinshuai,Xu, Hai-Chao
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supporting information
p. 12732 - 12735
(2017/09/14)
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- Preparation of Quinazolines via a 2+2+2 Annulation from Aryldiazonium Salts and Nitriles
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A (2+2+2) modular synthesis of multisubstituted quinazolines has been realized by the direct reaction of aryldiazonium salts with two equivalent of nitriles. Reaction of aryldiazonium salt with a nitrile provides the initial formation of a reactive nitrilium ion, which is attacked by another molecule of nitrile followed by electrophilic cyclization to deliver the desired product. Notable flexibility in the substitution patterns, readily available substrates, short reaction time, transition metal-free, and gram-scale synthesis are the advantages of this method.
- Ramanathan, Mani,Liu, Shiuh-Tzung
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p. 8290 - 8295
(2017/08/14)
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- Ruthenium-Catalyzed Enantioselective Hydrogenation of Phenanthridine Derivatives
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The first asymmetric hydrogenation of phenanthridines catalyzed by chiral cationic ruthenium diamine complexes has been developed with up to 92% ee and full conversions. The choice of the counteranion of the catalyst was found to be critical for achieving high enantioselectivity. In addition, the obtained 5,6-dihydrophenanthridine could be used as a chiral hydride donor for organocatalytic asymmetric transfer hydrogenation.
- Yang, Zhusheng,Chen, Fei,Zhang, Shuxin,He, Yanmei,Yang, Nianfa,Fan, Qing-Hua
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p. 1458 - 1461
(2017/03/23)
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- Assembly of substituted phenanthridines via a cascade palladium-catalyzed coupling reaction, deprotection and intramolecular cyclization
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The discovery and development of a general method for the one-pot synthesis of substituted phenanthridines is presented. In the presence of Pd(PPh3)4, accessible precursors undergo a Suzuki cross-coupling reaction with 2-(Boc-amino)benzeneboronic acid pinacol ester and then spontaneously undergo deprotection and intramolecular condensation to form the corresponding phenanthridines in one step. This reaction has a wide range of substrates with various functional groups, and the corresponding products have been obtained in good yields.
- Ge, Jun,Wang, Xiaojian,Liu, Tianqi,Shi, Zeyu,Xiao, Qiong,Yin, Dali
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p. 19571 - 19575
(2016/03/01)
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- Pd/Fe3O4 supported on nitrogen-doped reduced graphene oxide for room-temperature isocyanide insertion reactions
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A versatile Pd/Fe3O4 supported on N-doped reduced graphene oxide (N-rGO) catalyst was developed to carry out the synthesis of quinazolinones and phenanthridines under extremely mild conditions through isocyanide insertion cascades. T
- Singh, Karandeep,Singh, Ajay K.,Singh, Devendra,Singh, Rakhi,Sharma, Siddharth
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p. 3723 - 3726
(2016/06/14)
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- Pourbaix diagrams in weakly coupled systems: A case study involving acridinol and phenanthridinol pseudobases
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The thermodynamics of proton-coupled electron transfer (PCET) in weakly coupled organic pseudobases was investigated using 2,7-dimethyl-9-hydroxy-9-phenyl-10-tolyl-9,10-dihydroacridine (AcrOH) and 6-phenylphenanthridinol (PheOH) as model compounds. Pourba
- Walpita, Janitha,Yang, Xin,Khatmullin, Renat,Luk, Hoi Ling,Hadad, Christopher M.,Glusac, Ksenija D.
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p. 204 - 208
(2016/05/09)
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- NEW IRIDIUM-BASED COMPLEXES FOR ECL
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The present invention relates to novel iridium-based Ir(III) luminescent complexes, conjugates comprising these complexes as a label and their application, e.g. in the electrochemiluminescence based detection of an analyte.
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Paragraph 0199-0200
(2015/06/03)
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- NEW IRIDIUM-BASED COMPLEXES FOR ECL
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The present invention relates to novel iridium-based Ir(III) luminescent complexes, conjugates comprising these complexes as a label and their application, e.g. in the electrochemiluminescence based detection of an analyte.
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Paragraph 0215
(2015/06/03)
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- NEW IRIDIUM-BASED COMPLEXES FOR ECL
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The present invention relates to novel iridium-based Ir(III) luminescent complexes, conjugates comprising these complexes as a label and their application, e.g. in the electrochemiluminescence based detection of an analyte.
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Paragraph 0169-0170
(2015/06/03)
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- NEW BIS-IRIDIUM-COMPLEXES FOR MANUFACTURING OF ECL-LABELS
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The present invention relates to novel bis-iridium-based Ir(III) complexes, labels manufactured using these complexes and a method for producing such complexes.
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Paragraph 0113 - 0115
(2015/06/03)
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- Visible-light-promoted iminyl-radical formation from Acyl oximes: A unified approach to pyridines, quinolines, and phenanthridines
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A unified strategy involving visible-light-induced iminyl-radical formation has been established for the construction of pyridines, quinolines, and phenanthridines from acyl oximes. With fac-[Ir(ppy)3] as a photoredox catalyst, the acyl oximes were converted by 1 e- reduction into iminyl radical intermediates, which then underwent intramolecular homolytic aromatic substitution (HAS) to give the N-containing arenes. These reactions proceeded with a broad range of substrates at room temperature in high yield. This strategy of visible-light-induced iminyl-radical formation was successfully applied to a five-step concise synthesis of benzo[c]phenanthridine alkaloids.
- Jiang, Heng,An, Xiaode,Tong, Kun,Zheng, Tianyi,Zhang, Yan,Yu, Shouyun
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supporting information
p. 4055 - 4059
(2015/03/30)
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- Synthesis of allylated quinolines/isoquinolines via palladium-catalyzed cyclization-allylation of azides and allyl methyl carbonate
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A novel and efficient strategy for one-step synthesis of allylated quinolines and isoquinolines via palladium-catalyzed cyclization-allylation of azides and allyl methyl carbonate is developed for the first time. The results indicated that the regioselective synthesis of allyl- and diallyl-substituted quinolines/isoquinolines depends on different substituted groups at R1 and R4 positions, such as H or other groups. The reactions proceed smoothly in the presence of Pd(PPh3)4 and K3PO4 or NaOAc in DMF at 100°C to give the corresponding allyl- and diallyl-substituted quinolines and isoquinolines in good to high yields.
- Luo, Jiang,Huo, Zhibao,Fu, Jun,Jin, Fangming,Yamamoto, Yoshinori
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p. 3227 - 3235
(2015/03/18)
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- Preparation of Substituted Phenanthridines from the Coupling of Aryldiazonium Salts with Nitriles: A Metal Free Approach
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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
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p. 5329 - 5336
(2015/05/27)
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- Transition Metal-Free Oxidative Radical Decarboxylation/Cyclization for the Construction of 6-Alkyl/Aryl Phenanthridines
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A radical cascade decarboxylation/cyclization of 2-isocyanobiphenyls with aliphatic carboxylic acids as well as aromatic carboxylic acids under the transition metal-free conditions was reported. This process, which included formation of two new C-C bonds and cleavage of C-COOH bonds, afforded a novel and environmentally friendly approach to producing 6-alkyl/aryl phenanthridines with moderate to good yields.
- Lu, Shichao,Gong, Yaling,Zhou, Demin
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p. 9336 - 9341
(2015/09/28)
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- Metal-free radical oxidative decarboxylation/cyclization of acyl peroxides and 2-isocyanobiphenyls
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A metal-free radical oxidative decarboxylation/cyclization of acyl peroxides and 2-isocyanobiphenyls was achieved, leading to 6-aryl phenanthridines as well as 6-alkyl phenanthridines in moderate to good yields. The procedure featured simple conditions and was metal-free and base free. It represents a practical approach to access 6-aryl/alkyl phenanthridines.
- Pan, Changduo,Zhang, Honglin,Han, Jie,Cheng, Yixiang,Zhu, Chengjian
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supporting information
p. 3786 - 3788
(2015/03/30)
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- NEW IRIDIUM-BASED COMPLEXES FOR ECL
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The present invention relates to novel iridium-based Ir(III) luminescent complexes, conjugates comprising these complexes as a label and their application, e.g. in the electrochemiluminescence based detection of an analyte.
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Page/Page column 41
(2014/02/16)
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- NEW BIS-IRIDIUM-COMPLEXES FOR MANUFACTURING OF ECL-LABELS
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The present invention relates to novel bis-iridium-based Ir(III) complexes, labels manufactured using these complexes and a method for producing such complexes.
- -
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Page/Page column 23; 24
(2014/02/16)
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- NEW IRIDIUM-BASED COMPLEXES FOR ECL
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The present invention relates to novel iridium-based Ir(III) luminescent complexes, conjugates comprising these complexes as a label and their application, e.g. in the electrochemiluminescence based detection of an analyte.
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Page/Page column 36; 37
(2014/02/16)
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- PhI(OAc)2-BF3-OEt2mediated domino imine activation, intramolecular C-C bond formation and β-elimination: New approach for the synthesis of fluorenones, xanthones and phenanthridines
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PhI(OAc)2-BF3-OEt2mediated domino synthesis of biologically important fluorenones, xanthones and phenanthridines has been developed. The reaction proceeds through imine activation, intramolecular C-C bond formation and β-elimination. This journal is
- Sarkar, Satinath,Tadigoppula, Narender
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p. 40964 - 40968
(2015/02/05)
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- Arylative cyclization of 2-isocyanobiphenyls with anilines: One-pot synthesis of 6-arylphenanthridines via competitive reaction pathways
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A transition-metal-free method for the synthesis of C6 phenanthridine derivatives by arylative cyclization of 2-isocyanobiphenyls with arylamines in one pot was developed. Mechanistic studies suggest that electrophilic aromatic substitution (SEAr) of a nitrilium intermediate and homolytic aromatic substitution (HAS) of an imidoyl radical intermediate are two competitive reaction pathways involved in the annulation step.
- Xia, Zhonghua,Huang, Jinbo,He, Yimiao,Zhao, Jiaji,Lei, Jian,Zhu, Qiang
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p. 2546 - 2549
(2014/05/20)
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- Synthesis of phenanthridine derivatives via cascade annulation of diaryliodonium salts and nitriles
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A cascade coupling reaction toward a variety of phenanthridine derivatives has been developed. This cascade transformation proceeds via the copper-catalyzed coupling reaction of diaryliodonium salts and nitriles, and undergoes cyclization into the phenanthridine core.
- Li, Jian,Wang, Hongni,Sun, Jiangtao,Yang, Yang,Liu, Li
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p. 7904 - 7908
(2014/12/12)
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- Synthesis of polysubstituted phenanthridines via ligand-free copper-catalyzed annulation
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A novel procedure for the cascade reaction of the addition of a Grignard reagent to a nitrile with a copper-catalyzed C-N bond coupling was developed, which afforded various polysubstituted phenanthridines in moderate to good yields with tolerance for a wide variety of substrates. Experimental data demonstrated that the reaction proceeded more likely through a Cu(I/III) catalytic cycle.
- Chen, Yan-Fu,Hsieh, Jen-Chieh
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p. 4642 - 4645
(2015/01/08)
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- Synthesis of 6-substituted phenanthridines by metal-free, visible-light induced aerobic oxidative cyclization of 2-isocyanobiphenyls with hydrazines
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Irradiation of hydrazines with visible-light in the presence of organic dye eosin B generates various types of functional radicals, which are trapped by 2-isocyanobiphenyls to give 6-substituted phenanthridines. the Partner Organisations 2014.
- Xiao, Tiebo,Li, Linyong,Lin, Guoliang,Wang, Qile,Zhang, Ping,Mao, Zong-Wan,Zhou, Lei
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supporting information
p. 2418 - 2421
(2014/05/06)
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- Transition-metal-free, visible-light induced cyclization of arylsulfonyl chlorides with 2-isocyanobiphenyls to produce phenanthridines
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6-Aryl substituted phenanthridines were synthesized via a visible-light-catalyzed cyclization of 2-isocyanobiphenyls with arylsulfonyl chlorides under oxidant-free and transition-metal-free conditions. This transformation represents an efficient and attractive synthetic utilization of arylsulfonyl chlorides. the Partner Organisations 2014.
- Gu, Lijun,Jin, Cheng,Liu, Jiyan,Ding, Hongyan,Fan, Baomin
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supporting information
p. 4643 - 4645
(2014/05/06)
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- Direct, catalytic, and regioselective synthesis of 2-alkyl-, aryl-, and alkenyl-substituted N -Heterocycles from n -oxides
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A one-step transformation of heterocyclic N-oxides to 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles is described. The success of this broad-scope methodology hinges on the combination of copper catalysis and activation by lithium fluoride or magnesium chloride. The utility of this method for the late-stage modification of complex N-heterocycles is exemplified by facile syntheses of new structural analogues of several antimalarial, antimicrobial, and fungicidal agents.
- Larionov, Oleg V.,Stephens, David,Mfuh, Adelphe,Chavez, Gabriel
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supporting information
p. 864 - 867
(2014/03/21)
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- Pd-catalyzed assembly of phenanthridines from aryl ketone O-acetyloximes and arynes through C-H bond activation
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Pd-catalyzed annulation of aryne and aryl ketone O-acetyloxime via C-H bond activation was realized. Through the C-H bond activation/insertion/cyclization/ elimination reaction sequence, phenanthridines are successfully constructed, providing an attractiv
- Tang, Chen-Yu,Wu, Xin-Yan,Sha, Feng,Zhang, Fei,Li, Hao
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supporting information
p. 1036 - 1039
(2014/02/14)
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- Pd-catalyzed assembly of phenanthridines from aryl ketone O-acetyloximes and arynes through C-H bond activation
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Pd-catalyzed annulation of aryne and aryl ketone O-acetyloxime via C-H bond activation was realized. Through the C-H bond activation/insertion/cyclization/elimination reaction sequence, phenanthridines are successfully constructed, providing an attractive
- Tang, Chen-Yu,Wu, Xin-Yan,Sha, Feng,Zhang, Fei,Li, Hao
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supporting information
p. 1036 - 1039
(2015/02/19)
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- Bronsted acid-mediated reactions of aldehydes with 2-vinylaniline and biphenyl-2-amine
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Herein we report simple Bronsted acid-mediated reactions of aldehydes with 2-vinylaniline and biphenyl-2-amine. Ultimately, the useful nitrogen-containing heterocycle derivatives are obtained. The electronic properties of the substituents on the aldehydes and 2-vinylaniline were investigated. It was found that molecules with both electron-donating and -withdrawing substituents were perfectly suitable substrates for this transformation, and the expected products were obtained in moderate to excellent yields.
- Zhang, Xu,Xu, Xuefeng,Yu, Lintao,Zhao, Qiang
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supporting information
p. 2280 - 2282
(2014/04/17)
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