- Palladium-catalyzed phosphination and amination through C–H bond functionalization on biphenyl: Amido-substituent as directing group
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The formation of N-(2’-(diphenylphosphoryl)-[1,1′-biphenyl]-2-yl)-2,3,4,5,6-pentafluorobenzamide (3_eaaa) has been achieved through the palladium-catalyzed and Ag(I)-assisted C–H functionalization of N-([1,1′-biphenyl]-2-yl)-2,3,4,5,6-pentafluorobenzamide
- Kao, I-Hsiang,Wang, Ching-Yu,Chang, Yu-Chang,Wu, Chu-Lun,Chiu, Yu-Jen,Hong, Fung-E
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- Visible-light induced synthesis of 8H-indolo[3,2,1-de]phenanthridin-8-ones and related heterocycles using benzothiadiazole as photocatalyst
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A simple and mild approach to access polycyclic 8H-indolo[3,2,1-de]phenanthridin-8-ones through a visible-light induced free radical cyclization of (2-bromophenyl)(9H-carbazol-9-yl)methanones using benzothiadiazole-containing photocatalyst is reported. This transition metal free method can be utilized for the synthesis of 7H-thieno[2′,3′:4,5]pyrido[3,2,1-jk]carbazol-7-one, 14H-isoquinolino[4,3,2-kl]phenoxazin-14-one, 14H-isoquinolino[4,3,2-kl]phenothiazin-14-one, and 10,11,12,13-tetrahydro-8H-indolo[3,2,1-de]phenanthridin-8-one. Moreover, some products were found to emit strong blue or green fluorescence.
- Li, Hanjie,Lu, Ping,Qiao, Li,Wang, Yanguang,Zhang, Ke
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- Electrochemical Palladium-Catalyzed Intramolecular C—H Amination of 2-Amidobiaryls for Synthesis of Carbazoles
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The synthesis of carbazoles based on the electrochemical Pd-catalyzed intramolecular C—H amination of 2-amidobiaryls through oxidative cross coupling has been achieved under mild reaction conditions. The reaction can be carried out in undivided cell without the addition of external chemical oxidant. Besides good functional group compatibility, the desired carbazoles can be scaled up and modified easily. Compared with previous methods, this protocol affords a simple and sustainable avenue for the construction of carbazoles.
- Gao, Xinlong,Lei, Aiwen,Wang, Pan,Wang, Qingqing,Zhang, Heng,Zhang, Xiaojing
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supporting information
p. 143 - 148
(2020/12/18)
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- Method for the synthesis of 1-carbazole-boric acid pinacol ester by amide ortho-orthogonal directing borification
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The present invention discloses a method of synthesizing 1-carbazole - boronic acid pinacol ester by orthophoreinization of an amide orthostatic directional boronate, the steps comprising: (1) the carbazole and the amidation reagent under the action of a
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Paragraph 0044-0045
(2022/01/04)
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- 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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- X-ray excited ultralong room-temperature phosphorescence for organic afterglow scintillators
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We present X-ray-excitable organic ultralong room temperature phosphorescence (X-OURTP) for afterglow scintillators through implanting lone-pair electron involved n-π? transitions and efficient charge transfer characters into H-aggregations of organic cry
- Chen, Qiushui,Chen, Runfeng,Huang, Wei,Li, Huanhuan,Peng, Hao,Tang, Lele,Tao, Ye,Tian, Dan,Yan, Xi,Yang, Qingqing,Zan, Jie
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supporting information
p. 13559 - 13562
(2020/11/17)
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- N-Acylcarbazoles and N-Acylindoles: Electronically Activated Amides for N-C(O) Cross-Coupling by Nlpto Ar Conjugation Switch
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The development of new amide precursors for selective, catalytic activation of carbon-nitrogen bonds in amides is a fundamental objective of this emerging reactivity manifold. We report the palladium-catalyzed Suzuki-Miyaura cross-coupling of N-acylcarbazoles and N-acylindoles with arylboronic acids by a highly selective N-C(O) cleavage. The key amide bond ground-state destabilization stems from Nlp to Ar conjugation and enables us for the first time to achieve reactivity similar to that for N-acylsulfonamide and N-acylcarbamate activation in simple anilides.
- Buchspies, Jonathan,Rahman, Md. Mahbubur,Szostak, Roman,Szostak, Michal
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supporting information
p. 4703 - 4709
(2020/06/17)
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- Acyl-Directed ortho-Borylation of Anilines and C7 Borylation of Indoles using just BBr3
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Indoles are privileged heterocycles found in many biologically active pharmaceuticals and natural products. However, the selective functionalization of the benzenoid moiety in indoles in preference to the more reactive pyrrolic unit is a significant challenge. Herein we report that N-acyl directing groups enable the C7-selective C?H borylation of indoles using just BBr3. This transformation shows some functional-group tolerance and notably proceeds with C6 substituted indoles. The directing group can be readily removed in situ and the products isolated as the pinacol boronate esters. Acyl-directed electrophilic borylation can be extended to carbazoles and anilines with excellent ortho selectivity. 4-amino-indoles are amenable to this process, with acyl group installation and directed electrophilic C?H borylation enabling selective formation of C5-BPin-indoles.
- Iqbal, Saqib A.,Cid, Jessica,Procter, Richard J.,Uzelac, Marina,Yuan, Kang,Ingleson, Michael J.
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supporting information
p. 15381 - 15385
(2019/10/22)
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- TICT (twisted intramolecular charge transfer) triplet-state electroluminescent material and device
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The invention provides an electroluminescent material and an electroluminescent device utilizing the same as a luminous layer. The electroluminescent material comprises a compound represented in formula I in the description, wherein R1, R2, R3, R4 and R5
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Paragraph 0056-0059
(2019/09/17)
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- SELECTIVE INHIBITORS OF GENOTOXIC STRESS-INDUCED IKK/NF-kB PATHWAYS
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The invention relates to chemical compounds and their use as a medicament in the treatment of a disease associated with genotoxic stress-induced I KK/NF-κΒ (NF-kappaB) activation, preferably in the treatment of a subject suffering from cancer exhibiting g
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Page/Page column 86
(2018/05/27)
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- N-substituted carbazole-amide room temperature phosphorescent molecules and preparation method and application thereof
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The invention discloses a room temperature phosphorescent compound and a preparation method, a single crystal culture method and application thereof in the field of anti-counterfeit. According to the invention, through acylation reaction with the particip
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Paragraph 0031; 0032; 0033; 0035; 0036
(2017/10/31)
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- TFAA/H3PO4 mediated unprecedented N-acylation of carbazoles leading to small molecules possessing anti-proliferative activities against cancer cells
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For the first time TFAA/H3PO4 has facilitated the direct and metal-free N-acylation of carbazoles leading to a number of N-acylated derivatives. Several of these compounds were found to be promising when tested for their anti-proliferative properties against oral cancer cell lines. This journal is the Partner Organisations 2014.
- Kolli, Sunder Kumar,Prasad, Bagineni,Babu, P. Vijaya,Ashfaq, Mohd Ashraf,Ehtesham, Nasreen Z.,Raju, R. Ramesh,Pal, Manojit
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p. 6080 - 6084
(2014/08/05)
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- Decarboxylative acylation of indolines with α-keto acids under palladium catalysis: A facile strategy for the synthesis of 7-substituted indoles
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Palladium-catalyzed decarboxylative acylation of highly substituted indolines with α-keto acids via C-H bond activation is described. This protocol provides efficient access to C7-carbonylated indoles known to have diverse biological profiles. This journal is
- Kim, Minyoung,Kumar Mishra, Neeraj,Park, Jihye,Han, Sangil,Shin, Youngmi,Sharma, Satyasheel,Lee, Youngil,Lee, Eui-Kyung,Kwak, Jong Hwan,Kim, In Su
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supporting information
p. 14249 - 14252
(2014/12/11)
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- A palladium-catalyzed carbonylation approach to acid chloride synthesis
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We describe a new approach to acid chloride synthesis via the palladium-catalyzed carbonylation of aryl iodides. The combination of sterically encumbered phosphines (PtBu3) and CO coordination has been found to facilitate the rapid carbonylation of aryl iodides into acid chlorides via reductive elimination from (tBu3P)(CO) Pd(COAr)Cl. The formation of acid chlorides can also be exploited to perform traditional aminocarbonylation reactions under exceptionally mild conditions (ambient temperature and pressure), and with a range of weakly nucleophilic substrates.
- Quesnel, Jeffrey S.,Arndtsen, Bruce A.
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supporting information
p. 16841 - 16844
(2013/12/04)
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- Synthesis of N-acylcarbazoles through palladium-catalyzed aryne annulation of 2-haloacetanilides
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N-Acylcarbazoles have been synthesized in moderate to good yields by the annulation of in situ generated arynes with 2-haloacetanilides in the presence of a palladium catalyst and CsF. Both C-C and C-N bonds are formed simultaneously, and a variety of fun
- Lu, Chun,Markina, Nataliya A.,Larock, Richard C.
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p. 11153 - 11160
(2013/02/22)
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- Organocatalytic, oxidative, intramolecular C-H bond amination and metal-free cross-amination of unactivated arenes at ambient temperature
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The twinkling of an I: In a new atom-economical and environmentally friendly organocatalytic method for intramolecular C-H amination, the C-N bond forms at ambient temperature by abstraction of two atoms of hydrogen; only acetic acid and water are formed
- Antonchick, Andrey P.,Samanta, Rajarshi,Kulikov, Katharina,Lategahn, Jonas
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supporting information; experimental part
p. 8605 - 8608
(2011/11/05)
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- Intramolecular oxidative C-N bond formation for the synthesis of carbazoles: Comparison of reactivity between the copper-catalyzed and metal-free conditions
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New synthetic procedures for intramolecular oxidative C-N bond formation have been developed for the preparation of carbazoles starting from N-substituted amidobiphenyls under either Cu-catalyzed or metal-free conditions using hypervalent iodine(III) as an oxidant. Whereas iodobenzene diacetate or bis(trifluoroacetoxy)iodobenzene alone undergoes the reaction to provide carbazole products in moderate to low yields, combined use of copper(II) triflate and the iodine(III) species significantly improves the reaction efficiency, giving a more diverse range of products in good to excellent yields. On the basis of mechanistic studies including kinetic profile, isotope effects, and radical inhibition experiments, the copper species is proposed to catalytically activate the hypervalent iodine(III) oxidants. The synthetic utility of the present approach was nicely demonstrated in a direct synthesis of indolo[3,2-b]carbazole utilizing a double C-N bond formation.
- Cho, Seung Hwan,Yoon, Jungho,Chang, Sukbok
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supporting information; experimental part
p. 5996 - 6005
(2011/06/11)
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- Mo(CO)6-mediated carbamoylation of aryl halides
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A simple method for the synthesis of amides has been developed by molybdenum-mediated carbamoylation of aryl halides. Whereas the conventional palladium-catalyzed three-component coupling reaction requires a large excess of gaseous carbon monoxide, the incorporation of carbon monoxide in this Mo-mediated carbamoylation reaction is so efficient that it requires only a slight excess amount of carbon monoxide in the form of its molybdenum complex, Mo(CO)6. The reaction is applicable for the synthesis of a wide variety of not only secondary and tertiary amides but also primary amides by using aqueous ammonia.
- Ren, Wei,Yamane, Motoki
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experimental part
p. 8410 - 8415
(2011/02/23)
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- Palladium-catalyzed method for the synthesis of carbazoles via tandem C-H functionalization and C-N bond formation
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(Chemical Equation Presented) The development of a new method for the assembly of unsymmetrical carbazoles is reported. The strategy involves the selective intramolecular functionalization of an arene C-H bond and the formation of a new arene C-N bond. The substitution pattern of the carbazole product can be controlled by the design of the biaryl amide substrate, and the method is compatible with a variety of functional groups. The utility of the new protocol was demonstrated by the concise synthesis of three natural products from commercially available materials.
- Tsang, W. C. Peter,Munday, Rachel H.,Brasche, Gordon,Zheng, Nan,Buchwald, Stephen L.
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p. 7603 - 7610
(2008/12/22)
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- A versatile route to benzocanthinones
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Benzocanthinone (1) and five analogs (10, 12-15) were prepared by radical-induced cyclizations of halo N-aroyl derivatives of β-carboline and carbazole.
- Markgraf, J. Hodge,Dowst, Adrian A.,Hensley, Laurel A.,Jakobsche, Charles E.,Kaltner, Cindy J.,Webb, Peter J.,Zimmerman, Patrick W.
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p. 9102 - 9110
(2007/10/03)
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- 1-Benzoylazoles: An experimental (NMR and crystallography) and theoretical study
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Five N-benzoylazoles (imidazole, pyrazole, indole, benzimidazole and carbazole) have been prepared following modified literature procedures. Their NMR spectra in solution (1H, 13C and 15N) have been measured. The crystal structures of 1-benzoylindole and 9-benzoylcarbazole have been determined by X-ray crystallography and the corresponding 13C NMR spectra in the solid state have been measured by the CPMAS technique. Whereas 1-benzoylindole presents a standard behaviour, 9-benzoylcarbazole shows an unexpected 13C CPMAS spectrum with additional splittings. In order to understand this fact, the 1H and 13C NMR spectra in dimethylether at -143°C (130 K) have been recorded and ab initio calculations (RHF/6-311G**) carried out. The corresponding absolute shieldings (GIAO/RHF/6-311G**) together with the X-ray structure and the 13C chemical shifts at low temperature have been used to discuss the CPMAS spectrum. We propose that the supplementary splittings of this spectrum are due to its conglomerate structure.
- Claramunt,Cornago,Sanz,Santa-María,Foces-Foces,Alkorta,Elguero
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p. 199 - 212
(2007/10/03)
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- Oxidation of benzylamines to amides
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A convenient method for the conversion of tertiary benzylamines to benzamides by phase transfer oxidation is described. Yields are good. Regioselectivities are reported.
- Markgraf, J. Hodge,Sangani, Poorab K.,Finkelstein, Manuel
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p. 1285 - 1290
(2007/10/03)
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- Intramolecular Addition of Aryl Radicals to Carbon-Nitrogen Double Bonds
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Cyclisation of radicals 6a,b is highly regioselective towards a 5-exo process; 6-endo ring closure is a minor route and their ratio depends on the substituents.No ring expansion of the five-membered radical intermediates 7a,b was observed.Radicals 27a,b give rise to 5-exo cyclisation regiospecifically.A competitive 1,5-hydrogen shift leading to imidoyl radicals was noticed.An analogous behaviour is also exhibited by vinyl radicals when allowed to add to carbon-nitrogen double bonds.
- Gioanola, Milena,Leardini, Rino,Nanni, Daniele,Pareschi, Patrizia,Zanardi, Giuseppe
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p. 2039 - 2054
(2007/10/02)
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- Recent Work on the Synthesis of 3,6-Dibenzoylcarbazole
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By heating carbazole (1) with aluminum trichloride and benzoyl chloride four benzoylcarbazole derivatives were obtained: N-benzoylcarbazole (2), 1-benzoylcarbazole (3), 3-benzoylcarbazole (4) and 3,6-dibenzoylcarbazole (5).The complete characterization of benzoylcarbazole derivatives 2-5 was performed by physical and spectroscopical methods (mp, tlc Rf, glc Tr, uv, ir, 1H nmr, 13C nmr and ms).
- Bonesi, Sergio Mauricio,Erra-Balsells, Rosa
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p. 1035 - 1038
(2007/10/02)
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- PHOTO-FRIES REARRANGEMENTS IN N-SULPHONYL CARBAZOLES
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When photo-Fries rearrangements in N-sulphonyl carbazoles 1 in benzene or methanol smoothly afforded 1- and 3- sulphonylcarbazoles 2 and 3 respectively in 29-55percent yield, N-benzoylcarbazole 1d did not undergo similar rearrangements to give the expected products.
- Chakrabati, Amit,Biswas, Goutam K.,Chakraborty, D. P.
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p. 5059 - 5064
(2007/10/02)
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- STUDIES ON ENAMIDES PART-2 : A NOVEL PHOTOCHEMICAL SYNTHESIS OF 9H-INDOLOPHENANTHRIDIN-9-ONE, A BENZCANTHINE ANALOGUE
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The synthesis of 3-aroylcarbazoles and the unknown 1-aroylcarbazoles has been achieved by the photolysis of 9-aroylcarbazoles in polar solvent.Irradiation of 3(a-c) in non-polar solvent afforded regiospecifically 5(a-c), carbazole (1) and for the first time, 9H-indolophenanthridin-9-one (8) from 3b.The yield of 8 was significantly improved by UV exposure of 9-(2-iodobenzoyl)-carbazole (3e) in methanol and iodine, without providing any photomigrated product.
- Ghosh, Somnath,Datta, Diptendu Bhusan,Datta, Indira,Das, Tapas Kumar
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p. 3775 - 3786
(2007/10/02)
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- STUDIES ON ENAMIDES. PART- 1 : PHOTOCHEMICAL REARRANGEMENTS OF N-AROYLCARBAZOLES
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The synthesis of 1- and 3-aroylcarbazoles has been achieved by the photolysis of N-aroylcarbazoles alongwith the formation of carbazole and the rearranged product ratio is wavelength dependent.
- Ghosh, Somnath,Das, Tapas Kumar,Datta, Diptendu Bhusan,Mehta, Sangeeta
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p. 4611 - 4614
(2007/10/02)
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- NUCLEOPHILIC ADDITION OF CARBAZOLES TO VINYL ESTERS
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It has been shown that 3-X-6-Y-carbazoles react in the presence of basic catalysts with vinyl esters simultaneously in two directions to form 3-X-6-Y-N-(α-acyloxyethyl)carbazoles and the corresponding N-acylcarbazoles.The decisive influence of the tempera
- Shekhirev, Yu. P.,Lopatinskii, V. P.,Sutyagin, V. M.,Tuzovskaya, S. A.
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p. 1192 - 1197
(2007/10/02)
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