18929-62-9Relevant academic research and scientific papers
Synergistic Activation of Amides and Hydrocarbons for Direct C(sp3)–H Acylation Enabled by Metallaphotoredox Catalysis
Baik, Mu-Hyun,Choi, Seulhui,Hong, Soon Hyeok,Lee, Geun Seok,Won, Joonghee
, p. 16933 - 16942 (2020/08/03)
The utilizations of omnipresent, thermodynamically stable amides and aliphatic C(sp3)?H bonds for various functionalizations are ongoing challenges in catalysis. In particular, the direct coupling between the two functional groups has not been realized. Here, we report the synergistic activation of the two challenging bonds, the amide C?N and unactivated aliphatic C(sp3)?H, via metallaphotoredox catalysis to directly acylate aliphatic C?H bonds utilizing amides as stable and readily accessible acyl surrogates. N-acylsuccinimides served as efficient acyl reagents for the streamlined synthesis of synthetically useful ketones from simple C(sp3)?H substrates. Detailed mechanistic investigations using both computational and experimental mechanistic studies were performed to construct a detailed and complete catalytic cycle. The origin of the superior reactivity of the N-acylsuccinimides over other more reactive acyl sources such as acyl chlorides was found to be an uncommon reaction pathway which commences with C?H activation prior to oxidative addition of the acyl substrate.
Phenyl substituted pyridazine structure unit containing compounds and methods for their preparation and use
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, (2016/11/17)
The invention discloses compounds containing phenyl substituted pyridazine structural unit, and a preparation method and application thereof. The structural general formula of the compounds containing phenyl substituted pyridazine structural unit is disclosed as Formula I. The compounds disclosed as Formula I have proper nuclear magnetic detection; and in order to solve the problems of less research on near-infrared materials and deficiency in high-efficiency high-stability near-infrared luminescent materials at present stage, the invention provides a series of near-infrared luminescent materials containing phenyl substituted pyridazine structure. The compounds have the advantages of accessible raw material, simple preparation process and high overall yield, and have important application value for researching development and application of near-infrared materials.
Regioselective annulation of unsymmetrical 1,2-phenylenebis(diaryl/diheteroarylmethanol): A facile synthesis of anthracene, tetracene, and naphtho[b]thiophene analogues
Sivasakthikumaran, Ramakrishnan,Rafiq, Settu Muhammad,Sankar, Elumalai,Clement, J. Arul,Mohanakrishnan, Arasambattu K.
, p. 7816 - 7835 (2015/12/31)
A systematic study on the regioselective cyclization of benzene- and naphthalene-based unsymmetrical diols with HBr (33 %) in acetic acid at room temperature led to the formation of annulation products. By using this method, synthesis of a wide variety of anthracene, tetracene and naphtho[b]thiophene analogues was achieved in good to excellent yields. By employing HBr (33 %) in acetic acid as a catalyst for regioselective cyclization of unsymmetrical diols was very facile and devoid of commonly encountered dihydroisobenzofuran formation. Regioselective cyclization of benzene- and naphthalene-based unsymmetrical diols with HBr (33 %) in acetic acid at room temperature led to the formation of annulated arenes and heteroarenes in good to excellent yields.
Efficient near-infrared-emitting cationic iridium complexes based on highly conjugated cyclometalated benzo[g]phthalazine derivatives
Xin, Lijun,Xue, Jie,Lei, Gangtie,Qiao, Juan
, p. 42354 - 42361 (2015/05/20)
Two near-infrared- (NIR-) emitting cationic iridium(iii) complexes, [Ir(dpbpa)2(Bphen)]+PF6- (1) and [Ir(dtbpa)2(Bphen)]+PF6- (2), were rationally designed and synthes
Ortho-quinodimethane from anthracene epidioxide: Scope of the Diels-Alder reaction and mild preparation of naphthalene derivatives
Siret, Bernard,Albrecht, Sébastien,Defoin, Albert
, p. 1075 - 1079 (2015/01/08)
The thermal isomerisation of anthracene epidioxide 3 has been known to give phenylenedioxy-ortho-quinodimethane 5 as a reactive transient. We presented herein the scope of the Diels-Alder reaction of this transient 5 with some dienophiles. In addition, a mild synthesis of naphthalene derivatives has been developed via base-induced cleavage of the obtained Diels-Alder adducts.
The reaction of arynes with münchnones: Synthesis of isoindoles and azaisoindoles
Lopchuk, Justin M.,Gribble, Gordon W.
, p. 2809 - 2812 (2014/05/06)
Arynes derived from silyltriflate precursors undergo a smooth 1,3-dipolar cycloaddition with münchnones to furnish isoindoles and azaisoindoles in moderate to high yields. Modification of the fluoride source, solvent, and temperature allows for the selective generation of either isoindoles or benzanthracenimines, the latter of which serve as precursors to polycyclic aromatic hydrocarbons.
Synthesis and characterization of naphth-annelated thiophene analogs
Clement, J. Arul,Mohanakrishnan, Arasambattu K.
experimental part, p. 2340 - 2350 (2010/06/12)
Synthesis of symmetrical and unsymmetrical naphth-annelated thienyl heterocycles has been achieved via thionation of hydroxyketones/diketones using Lawesson's reagent. Photophysical studies of 1,3-disubstituted naphtho[c]thiophene analogs are presented. Electro-oxidative behavior of these naphtha-annelated thiophenes are investigated using cyclic voltammeter.
Facile Oxidation of Polycyclic Arenes and Acetylenic Hydrocarbons with Bis(pyridine)silver Permanganate and Bis(2,2'-bipyridyl)copper(II) Permanganate Under Mild and Neutral Conditions
Firouzabadi, H.,Sardarian, A. R.
, p. 946 - 948 (2007/10/02)
The title compounds are used for the oxidation of polycyclic arenes and acetylenic hydrocarbons in dichloromethane at room temperature.
o-Quinonid Compounds. Part 18. Stabilised 2,3-Naphthoquinodimethanes via Transient 1,3-Diphenylbenzinden-2-one
Jones, David W.,Pomfret, Alan,Wife, Richard L.
, p. 459 - 466 (2007/10/02)
1,3-Diphenylbenzinden-2-one (8) can be reversibly generated by thermolysis of its formal (?4s + ?4s)-dimer (11) which is itself available in 5 steps from benzindan-1,3-dione; (8) adds stereospecifically to cis- and trans-but-2-ene.Photodecarbonylation of the adducts (23), (21), and (22) derived by trapping (8) with norbornadiene, trimethylmaleimide, and the dienophile (24) gives the sterically stabilized 2,3-napththoquinodimethanes (29), (25), and (26) respectively.These are long-lived in fluid solution at 20 deg C and were characterised by u.v.-visible spectroscopy and as their adducts with 4-phenyltriazoline-3,5-dione (PTD). 1,3,4,9-Tetraphenylbenzinden-2-one (37) generated by reaction of its dibromide (10; X = O, Y = Br) with sodium iodide forms the formal (?6s + Π6s)-dimer (35).Dissociation of (35) in the presence of N-phenylmaleimide gives the adduct (15).
TRANSFORMATIONS THERMIQUES DES PHOTOOXYDES MESO DES ACENES-VI. CAS DES PHOTOOXYDES DE PENTACENES
Sparfel, D.,Gobert, F.,Rigaudy, J.
, p. 2225 - 2235 (2007/10/02)
Thermolysis of the meso-pentacenic photooxides 1P, 1dP and 1tP, in solution, brings about various isomerizations which appear strongly affected by the phenyl substituents.Thus the pentacene photooxide 1P gives only the bicyclic acetal 9P, beside pentacenequinone 5P in high ratio.With the photooxides 1dP of 6,13-diphenylpentacene and 1tP of 5,7,12,14-tetraphenylpentacene, the main products are the naphthocyclobutenic diethers 8dP and 8tP, which are formed in competition with the bicyclic acetals 9dP and 9tP and, in the first case, with an isomer of a new kind, the bis-naphthofuranic diether 13dP.These discrepancies are interpreted in terms of the effect of phenyl groups on the successive steps of the previously established isomerization process of meso-acenic photooxides. Comparative analysis of the chemical shifts of the central carbon atoms, in (13)C NMR, allows the unambiguous assignment of the structure of each isomer.
