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1.
Inside Cover: Regioselective Synthesis of Polyheterohalogenated Naphthalenes via the Benzannulation of Haloalkynes (Chem. Eur. J. 50/2015) 下载免费PDF全文
Dr. Dan Lehnherr Joaquin M. Alzola Dr. Emil B. Lobkovsky Prof. Dr. William R. Dichtel 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(50):17990-17990
2.
Hiroki Sato Michelle A. Blemker Garrett Hellinghausen Prof. Daniel W. Armstrong Jordan W. Nafie Prof. Sean T. Roberts Prof. Michael J. Krische 《Chemistry (Weinheim an der Bergstrasse, Germany)》2019,25(37):8719-8724
Cyclometalation of a triple helical N-doped phenylene cage prepared by ruthenium(0)-catalyzed diol–diene benzannulation delivers a chiral, conformationally constrained Ir(ppy)3 analogue. Like the parent complex, fac-Ir(ppy)3, the iridium-containing PAH-cage is phosphorescent, but displays enhanced resistance to oxygen quenching. 相似文献
3.
Dr. William G. Shuler Dr. Sai P. Parvathaneni Jacob B. Rodriguez Taylor N. Lewis Adam J. Berges Prof. Christopher J. Bardeen Prof. Michael J. Krische 《Chemistry (Weinheim an der Bergstrasse, Germany)》2021,27(15):4898-4902
Ruthenium-catalyzed butadiene-mediated benzannulation enabled the first synthesis of 3,10-(di-tert-butyl)rubicene and its N-doped derivatives as well as preliminary studies on their photophysical properties. Unlike the parent rubicene and 3,10-(di-tert-butyl)rubicene, which adopt classical herringbone-type packing motifs in the solid state, the N-doped congener 7 b displayed columnar packing with an alternating co-facial arrangement of aromatic and heteroaromatic substructures. 相似文献
4.
Dr. Sankar Rao Suravarapu Dr. Sai Prathima Parvathaneni Jon A. Bender Prof. Sean T. Roberts Prof. Michael J. Krische 《Chemistry (Weinheim an der Bergstrasse, Germany)》2020,26(33):7504-7510
The first application of ruthenium(0)-catalyzed 1,2-dione-diyne [2+2+2] cycloaddition to PAH construction is achieved by the precision synthesis of soluble diindenoperylenes (DIPs), the electronic structures of which were investigated using steady-state absorption and emission, transient absorption, cyclic voltammetry and time-dependent density functional theory 相似文献
5.
Non‐linear,cata‐Condensed,Polycyclic Aromatic Hydrocarbon Materials: A Generic Approach and Physical Properties 下载免费PDF全文
Barnaby T. Haire Kane W. J. Heard Dr. Mark S. Little Dr. Adam V. S. Parry Dr. James Raftery Dr. Peter Quayle Prof. Dr. Stephen G. Yeates 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(28):9970-9974
A generic approach to the regiospecific synthesis of halogenated polycyclic aromatics is made possible by the one‐ or two‐directional benzannulation reactions of readily available (ortho‐allylaryl)trichloroacetates (the “BHQ” reaction). Palladium‐catalysed cross‐coupling reactions of the so‐formed haloaromatics enable the synthesis of functionalised polycyclic aromatic hydrocarbons (PAHs) with surgical precision. Overall, this new methodology enables the facile mining of chemical space in search of new electronic functional materials. 相似文献
6.
Rhodium‐Catalyzed Oxidative Benzannulation of N‐Pivaloylanilines with Internal Alkynes through Dual C−H Bond Activation: Synthesis of Highly Substituted Naphthalenes 下载免费PDF全文
Dr. Xuan Zhang Dr. Xiaoqiang Yu Dr. Xiujuan Feng Prof. Dr. Yoshinori Yamamoto Dr. Abdulrahman I. Almansour Dr. Natarajan Arumugam Dr. Raju Suresh Kumar Prof. Dr. Ming Bao 《化学:亚洲杂志》2016,11(22):3241-3250
An efficient method was developed for the synthesis of highly substituted naphthalenes through rhodium‐catalyzed oxidative benzannulation of N‐pivaloylanilines with internal alkynes. The benzannulation reaction proceeded smoothly through dual C?H bond activation to produce the corresponding highly substituted naphthalene products in satisfactory to good yields. 相似文献
7.
Yun‐Hua Kung Yu‐Sung Cheng Chia‐Cheng Tai Wei‐Szu Liu Chien‐Chueh Shin Chih‐Chung Ma Yi‐Chan Tsai Tsun‐Cheng Wu Ming‐Yu Kuo Prof. Yao‐Ting Wu Prof. 《Chemistry (Weinheim an der Bergstrasse, Germany)》2010,16(20):5909-5919
This work describes the syntheses, crystal structures, photophysical properties, and electro‐chemical analyses of benzo[k]fluoranthene‐based linear acenes, together with ab initio density functional theory computations on them. The molecules were prepared in generally moderate to good yields through Pd‐catalyzed cycloadditions between 1,8‐diethynylnaphthalene derivatives and aryl iodides. This protocol is simpler and more efficient than conventional methods. The scope and limitations of this reaction were examined. The structures of compounds 4 hb , 15 ac , 17 ab , 19 ac , and 24 je were determined by X‐ray analysis; they are either bent or twisted, rather than planar. The photophysical and electrochemical properties of these cycloadducts were also investigated and compared with computational predictions based on density functional theory. 相似文献
8.
The mechanism of the bond-forming reaction between C(7)H(6) (2+) and C(2)H(2) to yield C(9) entities has been investigated by density functional theory calculations with close comparison with experimental data. It is shown that the reaction produces the C(9)H(6) (2+) and C(9)H(7) (2+) di-cations with geometries most probably derived from the indene skeleton. In comparison, the formation of linear structures of di-cations is much more energy-demanding and therefore appears improbable. 相似文献
9.
Regioselective Dihalohydration Reactions of Propargylic Alcohols: Gold‐Catalyzed and Noncatalyzed Reactions 下载免费PDF全文
Jarryl M. D'Oyley Dr. Abil E. Aliev Dr. Tom D. Sheppard 《Angewandte Chemie (International ed. in English)》2014,53(40):10747-10750
The regioselective conversion of propargylic alcohols into previously unreported α,α‐diiodo‐β‐hydroxyketones was achieved by treatment with N‐iodosuccinimide in the presence of a gold catalyst. The corresponding α,α‐dichloro‐β‐hydroxyketones were obtained by treatment with trichloroisocyanuric acid in the absence of a catalyst. The latter reaction can be extended to other alkynols. These transformations can be used to prepare potentially useful halogenated building blocks. Preliminary mechanistic studies suggest that the reaction involves participation of the acetonitrile solvent in the formation of a 5‐halo‐1,3‐oxazine intermediate. 相似文献
10.
Ji Ma Yubin Fu Evgenia Dmitrieva Fupin Liu Hartmut Komber Felix Hennersdorf Alexey A. Popov Jan J. Weigand Junzhi Liu Xinliang Feng 《Angewandte Chemie (International ed. in English)》2020,59(14):5637-5642
Three unprecedented helical nanographenes ( 1 , 2 , and 3 ) containing an azulene unit are synthesized. The resultant helical structures are unambiguously confirmed by X‐ray crystallographic analysis. The embedded azulene unit in 2 possesses a record‐high twisting degree (16.1°) as a result of the contiguous steric repulsion at the helical inner rim. Structural analysis in combination with theoretical calculations reveals that these helical nanographenes manifest a global aromatic structure, while the inner azulene unit exhibits weak antiaromatic character. Furthermore, UV/Vis‐spectral measurements reveal that superhelicenes 2 and 3 possess narrow energy gaps ( 2 : 1.88 eV; 3 : 2.03 eV), as corroborated by cyclic voltammetry and supported by density functional theory (DFT) calculations. The stable oxidized and reduced states of 2 and 3 are characterized by in‐situ EPR/Vis–NIR spectroelectrochemistry. Our study provides a novel synthetic strategy for helical nanographenes containing azulene units as well as their associated structures and physical properties. 相似文献
11.
Dr. Yonglong Xiao Prof. Joel T. Mague Prof. James P. Donahue Dr. Laura J. Wilson Dr. Christina M. Kraml Prof. Robert A. Pascal Jr. 《Chemistry (Weinheim an der Bergstrasse, Germany)》2020,26(38):8458-8464
1,2,3,4,5,6,7,8-Octaphenylphenanthrene ( 4 ) and decaphenylphenanthrene ( 5 ) were prepared by very short syntheses (two or three steps) from tetraphenylfuran and polybrominated benzene derivatives. The X-ray structures of compounds 4 and 5 show them to be quite crowded, with the phenanthrene cores twisted by about 40° due to the clash of the C4 and C5 phenyl groups. Compound 4 was resolved by chromatography on a chiral support, and its free energy of activation for racemization was determined to be 24.6 kcal mol−1 at 40 °C. Computational studies indicate that compound 5 has a racemization barrier approximately 6 kcal mol−1 lower than 4 , and thus 5 would not be configurationally stable at room temperature. 相似文献
12.
The Precise Synthesis of Phenylene‐Extended Cyclic Hexa‐peri‐hexabenzocoronenes from Polyarylated [n]Cycloparaphenylenes by the Scholl Reaction 下载免费PDF全文
Dr. Martin Quernheim Dr. Florian E. Golling Wen Zhang Dr. Manfred Wagner Dr. Hans‐Joachim Räder Dr. Tomohiko Nishiuchi Prof. Dr. Klaus Müllen 《Angewandte Chemie (International ed. in English)》2015,54(35):10341-10346
The longitudinal extension of cycloparaphenylenes (CPP) towards ultrashort carbon nanotubes (CNTs) is essential for the solution based bottom‐up synthesis of CNTs. Herein, the longitudinal extension of the CPP skeleton by the introduction of hexaphenylbenzene units towards polyarylated [n]CPPs is described. Further, the applicability of the Scholl reaction to selectively form graphenic sidewalls is demonstrated. The ring size and substitution patterns of the polyarylated [n]CPPs were varied to overcome strain‐induced side reactions during the oxidative cyclodehydrogenation and cyclic para‐hexa‐peri‐hexabenzocoronene trimers ([3]CHBCs) were selectively obtained. This concept is envisioned as an access to ultrashort carbon nanotubes subject to the condition that further benzene rings with the right connectivity will be inserted. 相似文献
13.
Marcus Richter Sebastian Hahn Dr. Evgenia Dmitrieva Dr. Frank Rominger Dr. Alexey Popov Prof. Dr. Uwe H. F. Bunz Prof. Dr. Xinliang Feng Dr. Reinhard Berger 《Chemistry (Weinheim an der Bergstrasse, Germany)》2019,25(5):1345-1352
Polycyclic aromatic azomethine ylides (PAMYs) are powerful building blocks in the bottom-up synthesis of internally nitrogen-containing polycyclic aromatic hydrocarbons (N-PAHs) through 1,3-cycloaddition reactions. In this work, the cycloaddition reaction of PAMYs to asymmetric ortho-quinones is presented, which, in contrast to the addition to symmetric para-quinones, facilitates subsequent condensation reactions and allows the synthesis of three helical N-PAHs with ullazine-quinoxaline ( UQ - 1 – 3 ) backbones. UQ - 1 and UQ - 2 possess two helical centers; however, single-crystal X-ray analysis together with the computational modeling of UQ - 3 elucidate the formation of only the thermodynamically most stable geometry with four helical centers in a (P,P,M,M) configuration. For the series UQ - 1 – 3 , the number of redox steps is directly correlated with the number of ullazine or quinoxaline units incorporated into the targeted molecular backbones. A detailed investigation of the spectroscopic and magnetic properties of the radical cation and anion as well as the dication and dianion species by in situ EPR/UV/Vis-NIR spectroelectrochemistry is provided. The excellent optical and redox properties combined with helical geometries render them possibly applicable as chiral emitter or ambipolar charge transport material in organic electronics. 相似文献
14.
Punita V. VyasAnjani K. Bhatt Gadde RamachandraiahAshutosh V. Bedekar 《Tetrahedron letters》2003,44(21):4085-4088
A simple and efficient procedure for chlorination and bromination of aromatic amines, hydrocarbons and naphthols by the action of aqueous hydrohalic acid and hydrogen peroxide is described. This environmentally clean and safe procedure involves in situ generation of the active halogen and its uncatalyzed reaction with the substrates in this study. 相似文献
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16.
IntroductionItiswellknownthatmolecularorbital (MO)theoryhasplayedanimportantroleinunderstandingvariouschemicalreactionsofpolycyclicaromatichydrocarbons .1Especially ,theDiels Alderreactionsofmanypolycyclicbenzenoidhydrocarbonswithmaleicanhydridehavebeens… 相似文献
17.
Hugo Amistadi-Revol Dr. Julian Garrec Dr. Nicolas Casaretto Dr. Sébastien Prévost 《European journal of organic chemistry》2023,26(24):e202300359
Herein, a regioselective bromination or chlorination reaction of 1-naphthaldehydes is described. Without additive, the palladium-catalyzed C−H halogenation showed a C8-regioselectivity, whereas the formation of an aromatic imine intermediate allowed a switch to a C2-reactivity. Mechanistic studies and DFT calculations were performed to explain the regioselectivity and the synthesized halogenated products were used as key building blocks to access polycyclic natural product skeletons. 相似文献
18.
The thermal reaction of phencyclone (2) with a 1:1 mixture of 1,8-pyrenequinone (4) and 1,6-pyrenequinone (5) yields 2:1 adducts only of compounds 2 and 4. The observed polycyclic aromatic hydrocarbon 8 is formed via double Diels-Alder addition of 2 to 4, and the polycyclic ketone 9 arises from a combination of Diels-Alder and hetero-Diels-Alder reactions of 2 and 4. In contrast, Lewis acid-catalyzed reactions of 2, 4, and 5 give 2:1 adducts only of 2 and 5. The chief product, polycyclic diketone 10, is derived from a double hetero-Diels-Alder addition of 2 to 5. X-ray analysis of compound 8 shows it to be an exceptionally large polycyclic aromatic arch, and the X-ray structure of 10 reveals it to be a chiral molecular tweezer. 相似文献
19.
Uncatalyzed,Regioselective Oxidation of Saturated Hydrocarbons in an Ambient Corona Discharge 下载免费PDF全文
Stephen T. Ayrton Rhys Jones David S. Douce Mike R. Morris R. Graham Cooks 《Angewandte Chemie (International ed. in English)》2018,57(3):769-773
Atmospheric pressure chemical ionization (APCI) in air or in nitrogen with just traces of oxygen is shown to yield regioselective oxidation, dehydrogenation, and fragmentation of alkanes. Ozone is produced from ambient oxygen in situ and is responsible for the observed ion chemistry, which includes partial oxidation to ketones and C?C cleavage to give aldehydes. The mechanism of oxidation is explored and relationships between ionic species produced from individual alkanes are established. Unusually, dehydrogenation occurs by water loss. Competitive incorporation into the hydrocarbon chain of nitrogen versus oxygen as a mode of ionization is also demonstrated. 相似文献
20.
Dr. Kazuhiko Adachi Shunsuke Hirose Dr. Yasuyuki Ueda Prof. Dr. Hidehiro Uekusa Prof. Dr. Toshiyuki Hamura 《Chemistry (Weinheim an der Bergstrasse, Germany)》2021,27(11):3665-3669
Thermal isomerization of cyclobutaphenanthrene to o-quinodimethane was investigated. Sterically congested substituents or electron-donating substituents on the four-membered ring promoted the ring-opening, affording o-quinodimethane in a relatively stable form. Isolation of the newly prepared o-quinodimethane allowed its structural elucidation and investigation of its potential reactivities. Dual [4+2] cycloaddition of an aryne and o-quinodimethane afforded tetrabenzopentacene, demonstrating the synthetic application of the isolated compound. 相似文献