76426-81-8Relevant articles and documents
Easy Access to Versatile Catalytic Systems for C?H Activation and Reductive Amination Based on Tetrahydrofluorenyl Rhodium(III) Complexes
Kharitonov, Vladimir B.,Runikhina, Sofiya A.,Nelyubina, Yulia V.,Muratov, Dmitry V.,Chusov, Denis,Loginov, Dmitry A.
, p. 10903 - 10912 (2021)
On the basis of the 1,2,3,4-tetrahydrofluorenyl ligand, a simple approach was developed to new effective rhodium catalysts for the construction of C?C and C?N bonds. The halide compounds [(η5-tetrahydrofluorenyl)RhX2]2 (2
Rhodaelectrocatalysis for Annulative C?H Activation: Polycyclic Aromatic Hydrocarbons through Versatile Double Electrocatalysis
Kong, Wei-Jun,Finger, Lars H.,Oliveira, Jo?o C. A.,Ackermann, Lutz
supporting information, p. 6342 - 6346 (2019/04/08)
Rapid access to structurally diversified polycyclic aromatic hydrocarbons (PAHs) in a controlled manner is of key significance in materials sciences. Herein, we describe a strategy featuring two distinct electrocatalytic C?H transformations for the synthesis of novel nonplanar PAHs. The combination of rhodaelectrooxidative C?H activation/[2+2+2] alkyne annulation of easily accessible boronic acids with electrocatalytic cyclodehydrogenation provided modular access to diversely substituted PAHs with electricity as a sustainable oxidant. The unique molecular topology as well as the photophysical and electronic properties of the thus obtained PAHs were fully analyzed. The unique power of this metallaelectrocatalysis method was demonstrated by the chemoselective assembly of synthetically useful iodo-substituted PAHs.
Iron-catalyzed annulation reaction of arylindium reagents and alkynes to produce substituted naphthalenes
Adak, Laksmikanta,Yoshikai, Naohiko
experimental part, p. 5167 - 5171 (2012/07/31)
We report here an iron-bisphosphine complex-catalyzed annulation reaction of an arylindium reagent and two alkyne molecules that affords a substituted naphthalene derivative in moderate to good yield. The reaction represents a new example of iron-catalyzed C-C bond forming reactions via C-H bond functionalization.
Synthesis of highly substituted acenes through rhodium-catalyzed oxidative coupling of arylboron reagents with alkynes
Fukutani, Tatsuya,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
experimental part, p. 2867 - 2874 (2011/05/28)
The rhodium-catalyzed oxidative 1:2 coupling reactions of arylboronic acids or their esters with alkynes smoothly proceed to produce the corresponding annulated products. Of special note, highly substituted, readily soluble, and tractable anthracene and tetracene derivatives can be obtained selectively from 2-naphthyl- and 2-anthrylboron reagents, respectively.
Rhenium- and manganese-catalyzed synthesis of aromatic compounds from 1,3-dicarbonyl compounds and alkynes
Kuninobu, Yoichiro,Nishi, Mitsumi,Kawata, Atsushi,Takata, Hisatsugu,Hanatani, Yumi,Salprima Yudha,Iwai, Aya,Takai, Kazuhiko
experimental part, p. 334 - 341 (2010/03/30)
(Chemical Equation Presented) We have succeeded in the development of three approaches to the synthesis of aromatic compounds from 1,3-dicarbonyl compounds and alkynes. The first approach is a manganese-catalyzed [2+2+2] cycloaddition between 1,3-dicarbonyl compounds, which have no substituents at the active methylene moiety, and terminal alkynes. This reaction proceeds with high regioselectivity when aryl acetylenes are employed as the alkyne component. The second approach is a rhenium- or manganese-catalyzed formal [2+1+2+1] cycloaddition between β-keto esters and two kinds of alkynes. In this reaction, the aromatic compounds are obtained by the following reaction sequence: (1) insertion of the first alkyne into a carbon-carbon single bond of a β-keto ester, (2) formation of 2-pyranones via intramolecular cyclization with the elimination of ethanol, and (3) Diels-Alder reaction between the formed 2-pyranone and the second alkyne. This reaction provides multisubstituted aromatic compounds in a regioselective manner. The third approach is a rheniumcatalyzed formal [2+2+1+1] cycloaddition reaction from two 1,3-diketones and one alkyne. In this reaction, the aromatic skeleton is constructed from three carbons of the first 1,3-diketone, two carbons of the alkyne, and one carbon of the second 1,3-diketone. 2009 American Chemical Society.
Synthesis of highly substituted naphthalene and anthracene derivatives by rhodium-catalyzed oxidative coupling of arylboronic acids with alkynes
Fukutani, Tatsuya,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
scheme or table, p. 5198 - 5201 (2009/12/29)
The rhodium-catalyzed oxidative 1:2 coupling reactions of arylboronic acids with alkynes effectively proceeds in the presence of a copper-air oxidant to produce the corresponding annulated products. Of special note, anthracene derivatives can be obtained
Rhenium-catalyzed synthesis of multisubstituted aromatic compounds via C-C single-bond cleavage
Kuninobu, Yoichiro,Takata, Hisatsugu,Kawata, Atsushi,Takai, Kazuhiko
supporting information; experimental part, p. 3133 - 3135 (2009/05/07)
(Chemical Equation Presented) A reaction between a β-keto ester and an acetylene in the presence of a rhenium complex, [ReBr(CO)3(thf)] 2, as a catalyst, provided a 2-pyranone derivative in excellent yield via retro-aldol reaction (C-C single bond cleavage). By adding an acetylene-bearing ester group(s) after the formation of 2-pyranones, an aromatization reaction proceeded and multisubstituted aromatic compounds were obtained in good to excellent yields.
METHOD FOR PRODUCING POLYSUBSTITUTED ACENE COMPOUND
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Page/Page column 25-26, (2008/06/13)
PROBLEM TO BE SOLVED: To provide a method for easily producing a polysubstituted acene compound using a reduced amount of a transition metal. SOLUTION: The polysubstituted acene compound (1) is produced by reacting an aromatic compound (2) with an acetylene compound (3a) and an acetylene compound (3b) in the presence of a 1st metal compound and a 2nd metal compound. In the formula, R1, R2, R3, R4, A1a, A2, A3 and A4a are each independently a hydrocarbon group or the like; X1 and X2 are each a halogen atom; the P ring is an aromatic ring; and n is an integer of 1-10.
PREPARATION OF NAPHTHALENE DERIVATIVES BY REACTION OF BENZYNES WITH TIOPHENE-1,1-DIOXIDES
Nakayama, Juzo,Kuroda, Masami,Hoshino, Masamatsu
, p. 1233 - 1236 (2007/10/02)
The reaction of benzynes with thiophene-1,1-dioxides afford the Diels-Alder cycloadducts which spontaneously lose sulphur dioxide to give the corresponding naphthalene derivatives in moderate yields.Further reaction of benzyne with naphthalenes yielding dibenzobarrelenes is observed in a few cases.
REACTIONS OF SUBSTITUTED PYRIDINIUM N-IMINES WITH BENZYNE: SYNTHESES OF PYRIDOINDAZOLES AND RELATED COMPOUNDS
Yamashita, Yoshiro,Hayashi, Takashi,Masumura, Mitsuo
, p. 1133 - 1136 (2007/10/02)
Reactions of benzyne with several pyridinium N-imines were examined. 2-o-Aminophenylpyridine derivatives 6, pyridoindazoles (7), indazoloquinoline (17), and indazoloisoquinoline (18) were obtained by the reactions of benzyne with the