- A New Strategy for the Synthesis of Axially Chiral Biaryl Compounds
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Axially chiral compounds can be synthesized in high atropisomeric purity by aryl coupling of a conformationally locked dihydroxy-stilbenoids, which are readily available via Sharpless asymmetric dihydroxylation of olefin precursors.
- Rawal, Viresh H.,Florjancic, Alan S.,Singh, Surendra P.
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- Synthesis of Naphthocyclobutenes from α-Naphthyl Acrylates by Visible-Light Energy-Transfer Catalysis
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Methyl (α-naphthyl) acrylates bearing an ortho-substituent with a hydrogen atom produce naphthocyclobutenes upon Ir(Fppy)3-mediated photosensitization. This reaction can be described as a carbon analogue of the Norrish-Yang reaction: upon triplet excitation of the acrylate a 1,5-HAT results in a 1,4-diradical which forms the cyclobutene. Diastereoselectivities up to >20:1 were observed for the ring-closure reaction.
- Peez, Theodor,Schmalz, Veronika,Harms, Klaus,Koert, Ulrich
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- Rh-Catalyzed Formal [3+2] Cyclization for the Synthesis of 5-Aryl-2-(quinolin-2-yl)oxazoles and Its Applications in Metal Ions Probes
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A facile and efficient strategy for the synthesis of 5-aryl-2-(quinolin-2-yl)oxazoles via rhodium-catalyzed formal [3+2] cyclization of 4-aryl-1-tosyl-1H-1,2,3-triazoles with quinoline-2-carbaldehydes has been described. The protocol employs mild conditions and offers good yields of diverse 2,5-aryloxazole derivatives with a broad reaction scope. It is amenable to gram-scale synthesis and easily transformation. Moreover, this 5-aryl-2-(quinolin-2-yl)oxazole skeleton is indeed a new fluorophore and its applications in metal ions probes are also investigated and showed fluorescent responses to mercury ion.
- Zhou, Tongtong,He, Xinwei,Zuo, Youpeng,Wu, Yuhao,Hu, Wangcheng,Zhang, Shiwen,Duan, Jiahui,Shang, Yongjia
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p. 621 - 626
(2021/02/12)
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- Tuning Flavin-Based Photocatalytic Systems for Application in the Mild Chemoselective Aerobic Oxidation of Benzylic Substrates
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New flavin-based photocatalytic systems used for chemoselective aerobic visible-light oxidations have been developed by tuning the flavin structure and reaction conditions. 1,3-Dimethyl-7-trifluoromethylalloxazine (2) and 10-butyl-3-methyl-7-trifluoromethylisoalloxazine (3) were shown to mediate the selective oxidation of benzyl alcohols to form aldehydes in the presence of Cs2CO3. Flavin 3 was superior in the oxidation of toluene derivatives to form aldehydes in the presence of trifluoroacetic acid. On the other hand, photooxidations provided by ethylene-bridged quaternary flavinium salt 1 gave the corresponding carboxylic acids. The usefulness of the developed catalytic systems using 1–3 was also demonstrated in the oxidation of secondary benzylic and aliphatic alcohols, and benzylic methylene groups to form the corresponding ketones. The systems have the advantage of a broad substrate scope and metal-free conditions, which distinguish them from the previously reported flavin photooxidation reactions.
- Tolba, Amal Hassan,Vávra, Franti?ek,Chudoba, Josef,Cibulka, Radek
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supporting information
p. 1579 - 1585
(2019/12/24)
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- Ruthenium-Catalyzed Atropoenantioselective Synthesis of Axial Biaryls via Reductive Amination and Dynamic Kinetic Resolution
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The unprecedented ruthenium-catalyzed atropoenantioselective reductive amination of aldehydes with alkylamines via a cascade transfer hydrogenation and dynamic kinetic resolution strategy is described. This protocol features broad substrate scope and good functional group tolerance and allows the rapid assembly of axially chiral biaryls in good to high yields with high to excellent enantioselectivities. In addition, such structural motifs may have potential applications in enantioselective catalysis as chiral ligands or catalysts.
- Guo, Donghui,Zhang, Jianwei,Zhang, Bei,Wang, Jian
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p. 6284 - 6288
(2018/10/05)
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- Synthesis of N-Substituted Condensed Tetrahydropyridine-Based Enaminones via Palladium-Catalyzed Intramolecular C–N Cross-coupling
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A number of β-enaminones with secondary amino group (alkyl, cyclopropyl, and aryl) were prepared from corresponding β-diketones. Two general protocols for their palladium-catalyzed intramolecular C–N cross-coupling were established to give corresponding N-substituted condensed tetrahydropyridines in good yields. The methodology is applicable for a wide variety of structural motifs. The work also extends the applicability of novel, recently established, palladium precatalysts to new substrates.
- Dou?ová, Hana,R??i?ková, Zdeňka,?im?nek, Petr
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p. 670 - 684
(2018/01/22)
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- Atropoenantioselective redox-neutral amination of biaryl compounds through borrowing hydrogen and dynamic kinetic resolution
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We report herein a novel atropoenantioselective redox-neutral amination of biaryl compounds triggered by a cascade of borrowing hydrogen and dynamic kinetic resolution under the cooperative catalysis of a chiral iridium complex and an achiral Br?nsted acid. This protocol features broad substrate scope and good functional-group tolerance, and allows the rapid assembly of axially chiral biaryl compounds in good to high yields and with high to excellent enantioselectivity.
- Zhang, Jianwei,Wang, Jian
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p. 465 - 469
(2017/12/15)
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- Atropoenantioselective Redox-Neutral Amination of Biaryl Compounds through Borrowing Hydrogen and Dynamic Kinetic Resolution
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We report herein a novel atropoenantioselective redox-neutral amination of biaryl compounds triggered by a cascade of borrowing hydrogen and dynamic kinetic resolution under the cooperative catalysis of a chiral iridium complex and an achiral Br?nsted acid. This protocol features broad substrate scope and good functional-group tolerance, and allows the rapid assembly of axially chiral biaryl compounds in good to high yields and with high to excellent enantioselectivity.
- Zhang, Jianwei,Wang, Jian
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p. 465 - 469
(2018/02/21)
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- NOVEL ORGANIC HETEROCYCLIC COMPOUND AND LIGHT-EMITTING DEVICE COMPRISING SAME
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The present invention relates to an organic light-emitting compound represented by [Chemical Formula A] and an organic light-emitting device. In Chemical Formula, A, X, Y, Z, and the substituents R1 to R8, and R11 to R20 are as defined in the specification.
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- Pd(0)-catalyzed intramolecular Heck reaction: A general route for fused oxepine derivatives
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A simple and facile approach for the synthesis of various structurally different tricyclic bent oxepine frameworks from a readily accessible precursor has been introduced. The synthesis of substituted oxepine derivative involved Pd(0)-catalyzed Heck reaction. This methodology enriches the literature for the large ring formation.
- Adak, Arup Kumar,Mandal, Arabinda,Manna, Susanta Kumar,Mondal, Suresh Kumar,Jana, Akash,Ghosh, Dipesh,Kundu, Debasish,Samanta, Shubhankar,Ray, Jayanta K.
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supporting information
p. 452 - 459
(2016/04/05)
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- Synthesis of acyclic ketones by catalytic, bidirectional homologation of formaldehyde with nonstabilized diazoalkanes. Application of a chiral diazomethyl(pyrrolidine) in total syntheses of erythroxylon alkaloids
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This work offers a catalytic approach to convergent ketone assembly based upon formal and tandem C-H insertion of diazoalkanes in the presence of limiting amounts of monomeric formaldehyde, which is easily generated as a gas by thermolysis of the inexpensive and abundant paraformaldehyde (～30 USD/kg). The method forms di-, tri-, and even tetrasubstituted acetones with high efficiency, and it has streamlined a synthesis of (-)-dihydrocuscohygrine in which the absolute stereochemistry of a proline-based starting material is preserved. Assisted by the advent of new protocols for hydrazone oxidation, we also provide full details on handling non-carbonyl-stabilized diazo compounds.
- Wommack, Andrew J.,Kingsbury, Jason S.
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p. 10573 - 10587
(2013/11/19)
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- Synthesis of precursors for large-diameter hemispherical buckybowls and precursors for short carbon nanotubes
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We report herein the synthesis of six precursor molecules for the rational synthesis of isomerically pure armchair, zigzag, or chiral single-walled carbon nanotubes (SWCNTs). The polycyclic aromatic hydrocarbons possess the required carbon connectivity for the generation of extended hemispherical buckybowls with predefined geometry through intramolecular cyclodehydrogenation. The precursors for the short carbon nanotubes and the large-diameter hemispherical buckybowls have potential for the rational initiation of single-chirality SWCNT growth on metal surfaces. The options for the construction of precursors for various SWCNT chiralities based on the suggested synthesis strategy are presented.
- Mueller, Andreas,Amsharov, Konstantin Yu.
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p. 6155 - 6164,10
(2020/09/16)
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- Inter- and intramolecular hydroacylation of alkenes employing a bifunctional catalyst system
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Based on a conceptually innovative bifunctional P,N ligand, an efficient protocol for the rhodium-catalyzed inter- and intramolecular hydroacylation of alkenes has been developed.
- Vautravers, Nicolas R.,Regent, Damien D.,Breit, Bernhard
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p. 6635 - 6637
(2011/06/27)
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- New fluorescent blue oled host and dopant materials based on the spirobenzofluorene
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New spiro[benzo[c]fluorene-7,9'-fluorene] (SBFF)-based blue host materials, 9-phenyl-SBFF (BH-4P) and 5,9-diphenyl-SBFF (BH-6DP), were successfully prepared by spiro-formation of 9-phenyl-7H-benzo[c]fluoren- 7-one with 2-bromobiphenyl via lithiation and reaction of 5,9-dibromo-SBFF with phenylboronic acid through the Suzuki reaction, respectively. Diphenyl-[4-(2-[1,1;4,1]terphenyl-4-yl-vinyl)-phenyl]-amine (BD-1) and N,N-diphenyl-N',N'-diphenyl-SBFF-5,9-diamine (BD-6DPA) were used as dopant materials. Blue OLEDs with the configuration ITO/N,N'-bis-[4-(di-m-tolylamino) phenyl]-N,N'-diphenylbiphenyl-4,4'-diamine (DNTPD)/ bis[N-(1-naphthyl)-N-phenyl] benzidine (NPB)/host:5% dopant/SFC-137/Al-LiF were prepared from the two host materials doped with BD-1 and BD-6DPA dopants and the devices composed of BH-4P and BH-6DP doped with BD-6DPA showed blue EL spectra at 458 and 463 nm at 7 V and luminance efficiencies of 4.58 and 4.88 cd/A, respectively.
- Lee, In-Ho,Gong, Myoung-Seon
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p. 1475 - 1482
(2011/12/14)
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- Palladium-catalyzed intramolecular C-H activation: A synthetic approach towards polycyclic aromatic hydrocarbons
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A simple and convenient synthetic protocol for the construction of polycyclic aromatic hydrocarbons has been developed. A variety of phenanthrene, benzo[c]phenanthrene and chrysene derivatives was synthesized via Pd-catalyzed intramolecular C-H activation followed by acid-catalyzed water elimination.
- Paul, Sunanda,Jana, Rathin,Ray, Jayanta K.
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scheme or table
p. 1463 - 1468
(2010/08/20)
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- Palladium-catalyzed one-pot Suzuki coupling followed by arylpalladium addition to aldehyde: A convenient route to fluoren-9-one derivatives
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Various fluoren-9-one derivatives were prepared efficiently by a one-pot reaction involving sequential Suzuki coupling of 2-bromophenyl boronic acid with 2-bromocarboxaldehyde followed by intramolecular arylpalladium addition to aldehyde.
- Paul, Sunanda,Samanta, Shubhankar,Ray, Jayanta K.
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scheme or table
p. 5604 - 5608
(2010/10/21)
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- Tetralones as precursors for the synthesis of 2,2′-disubstituted 1,1′-binaphthyls and related compounds
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Using tetralones as starting materials, the synthesis of biaryl compounds is described in this paper. The tetralones were initially converted into 1-bromo-3,4-dihydro-2-naphthalenecarbaldehydes before effecting aromatization into the corresponding naphthalenes. These products were then subjected to Suzuki-Miyaura cross-coupling reactions, with a variety of aromatic boronic acids containing substituents in the ortho position, to afford biaryl compounds. The biaryl compounds possess heteroatom containing substituents ortho to the newly formed biaryl axis.
- Moleele, Simon S.,Michael, Joseph P.,de Koning, Charles B.
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p. 10573 - 10580
(2008/12/23)
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- Synthesis of a new olefin polymerization catalyst supported by an sp 3-C donor via insertion of a ligand-appended alkene into the Hf-C bond of a neutral pyridylamidohafnium trimethyl complex
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A new living and isoselective propylene polymerization precatalyst was generated via the intramolecular insertion of a ligand-appended vinyl group into the Hf-C bond of a neutral pyridylamidohafnium trimethyl complex. The Royal Society of Chemistry.
- Domski, Gregory J.,Edson, Joseph B.,Keresztes, Ivan,Lobkovsky, Emil B.,Coates, Geoffrey W.
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supporting information; experimental part
p. 6137 - 6139
(2009/05/06)
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- Methodology for the synthesis of 1,2-disubstituted arylnaphthalenes from α-tetralones
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α-Tetralones were initially converted into 1-bromo- dihydronaphthalene-2-carbaldehydes and 1-bromo-naphthalene-2-carbaldehydes. These precursors were then subjected to Suzuki coupling reactions to afford 1,2-disubstituted aryldihydronaphthalenes and 1,2-disubstituted arylnaphthalenes, respectively. The former products were oxidized with DDQ to give 1,2-disubstituted arylnaphthalenes.
- Moleele, Simon S.,Michael, Joseph P.,De Koning, Charles B.
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p. 2831 - 2844
(2007/10/03)
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- Synthesis and cytotoxic activity of acronycine analogues in the benzo[c]pyrano[3,2-h]acridin-7-one and naphtho[1,2-b][1,7] and [1,10]-phenanthrolin-7(14H)-one series
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Condensation of 1-bromo-2-naphthalenecarboxylic acid (9) with 7-methoxy-2,2-dimethyl-2H-1-benzopyran-5-ylamine (13) followed by acid-mediated cyclization afforded 6-methoxy-3,3-dimethyl-3,14-dihydro-7H-benzo[c]pyrano[3,2- h]acridin-7-one (15), which was further methylated into 6-methoxy-3,3,14- trimethyl-3,14-dihydro-7H-benzo[c]pyrano[3,2-h]acridin-7-one (benzo[c]acronycine) (3) and 6,7-dimethoxy-3,3-dimethyl-3H-benzo[c]pyrano[3,2-h] acridine (4). Osmium tetroxide oxidation of 15 gave the (±)-cis-diol 16, which afforded the benzopyranoacridine and benzopyranoacridone esters 17-22 upon acylation. Condensation of 9 with suitable aminoquinolines 23-25 afforded the carboxylic naphthylquinolylamines 26-28. Cyclization gave the corresponding naphtho[1,2-b][1,10]-phenanthrolin-7(14H)-ones 29 and 30, and naphtho[1,2-b][1,7]-phenanthrolin-7(14H)-one 31, which were subsequently N-methylated to the desired 14-methylnaphtho[1,2-b][1,10] and [1,7]-phenanthrolinones 6, 7, and 8. Benzo[c]pyrano[3,2-h]acridin-7-one derivatives 3, 16, and 22 displayed cytotoxic activities within the same range of magnitude as acronycine itself, whereas 7-alkoxybenzo[c]pyrano[3,2-h]acridine and 7-acyloxybenzo[c]pyrano[3,2-h]acridine derivatives 4 and 17-21 were less active when tested against L1210 murine leukemia cells in vitro. Naphthophenanthrolinones 6-8 were devoid of significant antiproliferative activity, but compounds 29-31 bearing no substituent on the nitrogen atom at position 14 were more potent.
- Bongui, Jean-Bernard,Elomri, Abdelhakim,Cahard, Dominique,Tillequin, Francois,Pfeiffer, Bruno,Pierre, Alain,Seguin, Elisabeth
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p. 1540 - 1546
(2007/10/03)
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- Potent 4-aryl- or 4-arylalkyl-substituted 3-isoxazolol GABAA antagonists: Synthesis, pharmacology, and molecular modeling
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We have previously described a series of competitive GABAA antagonists derived from the low-efficacy partial agonist 5-(4-piperidyl)-3- isoxazolol (4-PIOL, 4). The 2-naphthylmethyl analogue, 4-(2-naphthylmethyl)-5- (4-piperidyl)-3-isoxazolol (5), provided affinity for the GABAA receptor site higher than that of the standard GABAA receptor antagonist, SR 95531 (3). Molecular modeling studies of these compounds exposed a cavity at the receptor recognition site capable of accommodating aromatic groups of substantial size in the 4-position in the 3-isoxazolol ring. Here we present a series of analogues of 5, with various substituents in different positions in the naphthyl ring system (6a-k), and compounds with aromatic substituents directly attached to the 4-position of the 3-isoxazolol ring (71-n). The compounds have been pharmacologically characterized using receptor-binding assays and electrophysiological whole-cell patch-clamp techniques. All of the tested compounds show affinity for the GABAA receptor site. While the 5-, 7-, and 8-bromo analogues, 6b-d, showed receptor affinities (Ki = 45, 109, and 80 nM, respectively) comparable with that of 5 (Ki = 49 nM), the 1-bromo analogue, 6a, provided the highest receptor affinity of the series (Ki = 10 nM). Introduction of a series of different substituents in the 1-position in the 2-naphthyl ring system led to compounds, 6c-k, with retained high affinity for the GABA A receptor (Ki = 16-250 nM). Introduction of a phenyl ring directly into the 4-position on the 3-isoxazolol ring gave a 41-fold increase in affinity relative to that of 4-PIOL. In whole-cell patch-clamp recordings from cultured cerebral cortical neurons, all of the tested compounds were able to inhibit the effect of the specific GABAA agonist isoguvacine, 6a showing antagonist potency (IC50 = 42 nM) markedly higher than that of 3 (IC50 = 240 nM). Molecular modeling studies, based on the compounds described, emphasized the importance of the distal ring in 5 for receptor affinity and the considerable dimensions of the proposed receptor cavity. Furthermore, the phenyl rings in 71 and in 6k were shown to represent highly favorable positions for an aromatic ring in previously unexplored receptor regions in terms of a pharmacophore model.
- Fr?lund, Bente,Jensen, Lars S.,Guandalini, Luca,Canillo, Carolina,Vestergaard, Henrik T.,Kristiansen, Uffe,Nielsen, Birgitte,Stensb?l, Tine B.,Madsen, Christian,Krogsgaard-Larsen, Povl,Liljefors, Tommy
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p. 427 - 439
(2007/10/03)
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- One pot Sonogashira-coupling/Wittig olefination procedures
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Bromoarylcarbaldehydes, bromoheteroarylcarbaldehydes, and bromoalkenals can be subjected to a one pot Sonogashira coupling-Wittig olefination reaction to give easy access to molecules with extended pi-systems.
- Watanabe, Masataka,Mataka, Shuntaro,Thiemann, Thies
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p. 636 - 639
(2007/10/03)
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- A convenient and selective synthesis of unsymmetrical benzoins via the cyanide ion catalyzed cleavage of benzils
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The cyanide ion-catalyzed cleavage of benzils is used for the generation of various 'masked' acyl intermediates. The reaction of these intermediates with various aldehydes furnishes the corresponding esters of unsymmetrical benzoins in very good yields. A variety of unsymmetrical benzoin derivatives are synthesized in this way, including ferrocene derivatives. The hydrolysis of benzoin esters and their subsequent oxidation affords the corresponding unsymmetrical benzoins and benzils in high yield.
- Demir, Ayhan S.,Reis, ?mer
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p. 3803 - 3811
(2007/10/03)
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- A highly active Suzuki catalyst for the synthesis of sterically hindered biaryls: Novel ligand coordination
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A catalyst system for the preparation of biaryls containing four ortho substituents via Suzuki coupling is described. The combination of a catalytic quantity of Pd2(dba)3 with either an electron-rich biarylphosphine or DPEPhos is effective using a wide range of substrates. The X-ray crystal structure of (dba)Pd(2-(9-phenanthryl)phenyl-dicyclohexylphosphine), in which the Pd is coordinated to the 9,10-double bond of the phenanthryl group, is also reported. Copyright
- Yin, Jingjun,Rainka, Matthew P.,Zhang, Xiao-Xiang,Buchwald, Stephen L.
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p. 1162 - 1163
(2007/10/03)
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- Atroposelective attack of nucleophiles on 2-formyl-1-naphthamides and their derivatives: Chelation and non-chelation control
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Organometallic nucleophiles attack 2-formyl-1-naphthamides to give secondary alcohols with widely varying atroposelectivity. By careful choice of reagent, selectivities of up to >99:1 in favour of either the anti or the syn atropisomer can be obtained. Ethers and amines may be synthesised atroposelectively from acetals or imines. The sense of the selectivity is determined by the reactive conformation of the Ar-CHO bond, itself dependent on the coordinating and chelating ability of the nucleophile's counterion. The roles of conformation, Lewis acids, and chelation/non-chelation control in relation to stereoselectivity are discussed.
- Clayden, Jonathan,McCarthy, Catherine,Westlund, Neil,Frampton, Christopher S.
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p. 1363 - 1378
(2007/10/03)
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- The Preparation and Reactions of Naphthofuran and Naphthofuran
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The syntheses of 1,3-dihydro-1- and 1,3-dihydro-3-hydroxynaphthofuran are described.Upon treatment with acid, these compounds undergo 1,4-elimination of water to generate the reactive naphthofuran, which is trapped in situ by a variety of dienophiles.Aromatization of the resulting adducts gives access to 2,3-disubstituted phenanthrenes or benzanthracenes.In addition, it has been shown that the hemiacetal, 1,3-dihydro-1-hydroxynaphthofuran, which exists in tautomeric equilibrium with 3-(hydroxymethyl)-2-naphthaldehyde, serves as a convenient source of naphthofuran.This furan can also be trapped by a variety of dienophiles.The resulting Diels-Alder adducts can be aromatized, giving substituted anthracenes.The use of aromatic 1,4-quinones as dienophiles leads to linear polycyclic aromatic quinones of four to seven rings.
- Smith, James G.,Dibble, Peter W.,Sandborn, Richard E.
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p. 3762 - 3768
(2007/10/02)
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- A Novel Clathrate Design: Selective Inclusion of Uncharged Molecules via the Binaphthyl Hinge and Appended Coordinating Groups. X-ray Crystal Structures and Binding Modes of 1,1'-Binaphthyl-2,2'-dicarboxylic Acid Host/Hydroxylic Guest Inclusions
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1,1'-Binaphthyl-2,2'-dicarboxylic acid (1) is demonstrated as a novel type of clathrate host whose main mode of action is derived from a combination of the steric barrier and the coordinative interaction principle which constitutes the new "coordinatoclathrate" strategy.Inclusion properties of the crystal lattice of 1 are revealed for a variety of uncharged organic guest molecules (30 examples), ranging from OH-, to NH-, to CH-acidic compounds such as alcohols, carboxylic acids, amides, and nitriles to rather unpolar compounds like bromobenzene and toluene.Marked discrimination selectivities in the clathrate formation from solvent mixtures are found in regard to the group functionality, the substitution pattern, and the molecular size of the guest species, making accessible a simple process for chemical compound separation.The stoichiometries and the increased-temperature as well as the reduced-pressure stabilities of the various clathrates are discussed.The principles of stucture of five different alcohol clathrates of 1 are determined with the aid of X-ray structure analysis at 273 K: 1*2MeOH (10) 1/n, a = 15.642 Angstroem, b = 14.532 Angstroem, c = 9.292 Angstroem, β = 95.14 deg, Z = 4>; 1*2EtOH (11) ; 1*2(2-PrOH) (13) ; 1*2-BuOH (15) 1/n, a = 12.009 Angstroem, b = 12.747 Angstroem, c = 14.982 Angstroem, β = 105.52 deg, Z = 4>; 1*ethylene glycol (24) 1/n, a = 14.276 Angstroem, b = 9.533 Angstroem, c = 15.556 Angstroem, β = 109.19 deg, Z = 4>.In all these cases, however, hydroxyl groups of the host molecules were found to be intercalated via large pseudo-ring formation between the carboxyl functions of at least two host units of opposite chirality with a different mode of hydrogen bridging.Depending on the host:guest stoichiometry (1:1 or 1:2) and on the nature of the guest molecules, these entities consist of three, four, or eight moieties (COOH, OH).The direction of the strong and cooperative bonds is always homodromic.The shape and the size of the cleft formed in the matrix of cooperating host moieties are shown to vary, matching the specific needs of coordinating interactions (hydrogen bonding) and topological requirements (branching, e.g.) of the guest species.
- Weber, Edwin,Csoregh, Ingeborg,Stensland, Brigitta,Czugler, Matyas
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p. 3297 - 3306
(2007/10/02)
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