19222-81-2

Upstream product

• 108-37-2 1-bromo-3-chlorobenzene 
• 86-74-8 9H-carbazole 
• 625-99-0 3-iodochlorobenzene 
• 625-98-9 3-chlorofluorobenzene 
• 13029-09-9 2,2'-dibromobiphenyl 
• 108-42-9 3-chloro-aniline 

Downstream Products

• 870119-58-7 9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)phenyl)-9-hydrogencarbazole 

Relevant academic research and scientific papers

A waste-minimized protocol for copper-catalyzed Ullmann-type reaction in a biomass derived furfuryl alcohol/water azeotrope

We report the use of biomass-derived furfuryl alcohol as an effective bidentate ligand able to promote the Ullmann-type copper-catalyzed coupling of aryl halides with heteroaromatic or aliphatic amines. Furfuryl alcohol (FA) can be mixed with water to form the corresponding azeotrope (20 wt% of FA) and therefore can be easily recovered and reused. This protocol is efficiently applied to substrates with various electronic nature and affords the expected products (27 examples) in generally good to excellent yields. It has also been demonstrated that the protocol is both chemically and environmentally effective as the azeotropic mixture can be easily and almost quantitatively recovered at the end of the process.

COMPOUND, COMPOSITION, ORGANIC OPTOELECTRONIC DIODE, AND DISPLAY DEVICE

Disclosed are a compound represented by Chemical Formula 1, a composition comprising the same, an organic optoelectronic diode, and a display device. Chemical formula 1 is as defined in the specification.

Aryl Amination Using Soluble Weak Base Enabled by a Water-Assisted Mechanism

The amination of aryl halides has become one of the most commonly practiced C-N bond-forming reactions in pharmaceutical and laboratory syntheses. The widespread use of strong or poorly soluble inorganic bases for amine activation nevertheless complicates the compatibility of this important reaction class with sensitive substrates as well as applications in flow and automated synthesis, to name a few. We report a palladium-catalyzed C-N coupling using Et3N as a weak, soluble base, which allows a broad substrate scope that includes bromo- and chloro(hetero)arenes, primary anilines, secondary amines, and amide type nucleophiles together with tolerance for a range of base-sensitive functional groups. Mechanistic data have established a unique pathway for these reactions in which water serves multiple beneficial roles. In particular, ionization of a neutral catalytic intermediate via halide displacement by H2O generates, after proton loss, a coordinatively unsaturated Pd-OH species that can bind amine substrate triggering intramolecular N-H heterolysis. This water-assisted pathway operates efficiently with even weak terminal bases, such as Et3N. The use of a simple, commercially available ligand, PAd3, is key to this water-assisted mechanism by promoting coordinative unsaturation in catalytic intermediates responsible for the heterolytic activation of strong element-hydrogen bonds, which enables broad compatibility of carbon-heteroatom cross-coupling reactions with sensitive substrates and functionality.

Site-Selective N-Arylation of Carbazoles with Halogenated Fluorobenzenes

A method for the highly site-selective C-N bond-formation reaction of halogenated fluorobenzenes with carbazoles is described. The selectivity of iodine and fluorine atoms on the aromatic ring of fluorinated iodobenzenes was initially determined with a copper-N,N-diisopropylethylamine catalytic system. By changing the position of the iodine atom on the aromatic ring from the 3- or 4-position to the 2-position, the preferred coupling site was switched from the iodine atom to the fluorine atom. Steric hindrance of the fluorinated iodobenzenes is responsible for the selectivity switch. After elucidating the reaction mechanisms of these reaction processes, a metal-free method for the highly site-selective C-N bond-formation reaction of halogenated fluorobenzenes with carbazoles was revealed through C-F bond activation. The metal-free system is able to handle a range of halogenated groups. Thus, a broad range of chlorinated, brominated, and iodinated N-arylated carbazoles were generated, which are widely useful in organic chemistry.

An Efficient Synthesis of N-(Hetero)arylcarbazoles: Palladium-Catalyzed Coupling Reaction between (Hetero)aryl Chlorides and N-Carbazolylmagnesium Chloride

An efficient method for the synthesis of N-(hetero)arylcarbazoles, useful compounds for functional materials, is reported. Various (hetero)aryl chlorides reacted with N-carbazolylmagnesium chloride in the presence of a palladium catalyst (0.05 to 0.2 mol%) prepared from allylpalladium(II) chloride dimer {[PdCl(allyl)]2} and di-tert-butyl(2,2-diphenyl-1-methylcyclopropan-1-yl)phosphine (cBRIDP) under mild conditions (110°C) in a short period of time (15 min to 2 h) to give N-(hetero)arylcarbazoles in high yields. The reactions of bromochlorobenzenes proceeded in favour of the bromo group to afford N-(chlorophenyl)carbazoles in a highly selective manner. Functional materials for use in organic light-emitting diodes, such as mCP, 26mcPy, CBP and TCB, were also obtained in high yields within 15 min by the reaction of (hetero)aryl polyhalides. Optimization of the reaction conditions and a postulated catalytic cycle for the reaction are also discussed.

PHOSPHORUS COMPOUND AND TRANSITION METAL COMPLEX OF THE SAME

The present invention provides a compound represented by general formula (1) and a transition metal complex containing the compound as a ligand: wherein R1 to R10, N, P, Y, and Z have the meanings as defined in DESCRIPTION.

REACTION CATALYST FOR CROSS COUPLING AND METHOD FOR MANUFACTURING AROMATIC COMPOUND

The object of the present invention is to provide a new organic phosphorus ligand that can efficiently promote cross-coupling reaction to obtain the target substance at high yield, as well as a method of manufacturing such ligand whose steric characteristics and electronic characteristics can be fine-tuned and which can be used to cause cross-coupling reaction at high yield. As a means for achieving the aforementioned object, a phosphine compound expressed by General Formula (1) below is provided. (In the formula, R1 and R2 are each independently a secondary alkyl group, tertiary alkyl group, or cycloalkyl group, while R3 and R4 are each independently a hydrogen, aliphatic group, heteroaliphatic group, aromatic group, alicyclic group, or heterocyclic group. Note that R3 and R4 have no phosphorus atom and that R3 and R4 are not both hydrogen at the same time).

COMPOUND, ORGANIC LiGHT EMITTING DIODE INCLUDING THE SAME AND DISPLAY INCLUDING THE ORGANIC LiGHT EMITTING DIODE

The purpose of the present invention is to provide a compound realizing an organic photoelectronic diode having properties such as high efficiency, long life, etc. The present invention relates to a compound, an organic light emitting diode including the same, and a display device including the organic light emitting diode. The compound is represented by chemical formula 1.COPYRIGHT KIPO 2015

CONDENSED CYCLIC COMPOUND, AND ORGANIC LIGHT EMITTING DEVICE INCLUDING THE SAME

Disclosed are a condensed ring compound and an organic light emitting device comprising the condensed ring compound. The organic light emitting device comprises: a first electrode; a second electrode facing the first electrode; and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises the condensed ring compound.COPYRIGHT KIPO 2015

Copper/β-diketone-catalysed N-arylation of carbazoles

A copper-catalysed C-N bond-forming reaction of carbazoles with aryl iodides is described. Several commercially available ligands such as β-diketone and diamine, are tested in the N-arylation of carbazoles. The catalytic system generated in situ from an inexpensive copper salt, simple β-diketone and inorganic base efficiently N-arylated the carbazoles. A wide range of aryl iodides and carbazoles can be coupled to generate N-arylcarbazoles in the presence of various functional groups. However, the sterically hindered effect of aryl iodides is evident in this catalytic system. The selectivity of two iodine atoms on the aromatic ring of diiodobenzene is evaluated in the developed catalytic system. Results showed that the selectivity of diiodobenzene can be tuned by the reaction temperature.