84716-37-0

Upstream product

• 109-97-7 pyrrole 
• 21792-52-9 1,2-diethynylbenzene 
• 86-53-3 1-Cyanonaphthalene 
• 703-55-9 1-naphthylmagnesiumbromide 
• 13922-41-3 1-Naphthylboronic acid 
• 90-11-9 1-Bromonaphthalene 
• 135884-31-0 N-boc-2-pyrroleboronic acid 
• 90-14-2 1-Iodonaphthalene 
• 36216-15-6 4-methyl-N-(naphthalen-1-ylmethylene)benzenesulfonamide 
• 4653-13-8 4-(1-naphthyl)-4-oxobutanoic acid 
• 941-98-0 1'-naphthacetophenone 
• 906560-16-5 5-naphthalen-1-yl-3H-furan-2-one 
• 910472-00-3 4-(naphthalen-5-yl)-4-oxobutanal 
• 215187-31-8 N-tert-butyloxycarbonyl-2-(1'-naphthyl)pyrrole 

Downstream Products

• 1277091-04-9 4,4-difluoro-3,5-di(naphth-1-yl)-8-mesityl-4-bora-3a,4a-diaza-s-indacene 

Relevant academic research and scientific papers

Pyrrolic Type N Directed Borylation Route to BN-PAHs: Tuning the Photophysical Properties by Varying the Conjugation Shape and Size

Two series of BN-cyclopenta[a]phenalenes have been synthesized through an indole/pyrrole oriented borylation reaction. A total of five compounds are obtained and fully characterized; one of them is unambiguously confirmed by single X-ray crystal structure. Their photophysical properties could be finely tuned through varying the conjugation size and shape of the bottom PAHs applied. Moreover, their response toward fluoride anions was also investigated.

Boron-nitrogen-doped polycyclic conjugated aromatic hydrocarbon embedded with pyrrole unit and synthesis method thereof

The invention aims to provide a design and synthesis method of novel boron-nitrogen doped polycyclic aromatic hydrocarbon and potential application thereof, and provides more schemes for obtaining more efficient organic photoelectric materials. In order to achieve the purpose, the technical scheme adopted by the invention is as follows: indole or pyrrole derivatives are used as raw materials, boron-nitrogen doped macroconjugated polycyclic aromatic hydrocarbon and derivatives thereof at specific positions are generated by nitrogen guidance, and the structural formula of the compounds is shownin the specification; in the formula, R1 is independent, can be alkane, and can also be substituted or unsubstituted aryl or heteroaryl, the R2, R3, R4, R5, R6, R7, R8, R9 and R10 are independent, canbe substituted or unsubstituted aryl, heteroaryl, alkane, cycloalkane, olefin and alkyne, and can also be hydrogen or a single substituted halogen atom X (F, Cl, Br and I), the R11, R12, R13, R14 andR15 are independent, can be substituted or unsubstituted aryl, heteroaryl, alkane, cycloalkane, olefin and alkyne, and can be hydrogen, alkyl, aldehyde group or ketone, the Ar1, Ar4 and Ar5 aryl arerespectively a benzene ring, a thiophene ring, a furan ring, pyrrole, pyridine, benzothiophene, benzofuran, benzopyrrole, benzopyridine, a naphthalene ring, an anthracene ring, phenadiene, tetracene,pyrene, and linear or angled pentacene, hexacene, indene or fluorene, and the Ar2 and Ar3 aryl groups are benzene rings and substituted benzene rings.

Effects of π-extension on pyrrole hemithioindigo photoswitches

The most red-shifted hemithioindigo photoswitches have been identified through systematic introduction of aryl units to a parent pyrrole hemithioindigo photoswitch. Increasing the size of the 5′-aryl substituent is ineffective at producing further redshif

BIARYL LIGANDS

Embodiments of the present disclosure provide for biaryl ligands (also referred to herein as "biaryl compound"), biaryl complexes, methods of making biaryl compounds, methods of making single enantiomers of these biaryl compounds, methods of use (e.g., ca

Triethanolamine-mediated palladium-catalyzed regioselective C-2 direct arylation of free NH-pyrroles

An atom-economical phosphane-free palladium-catalyzed direct C-2 arylation of unactivated free NH-pyrroles is devised. This method provides a straithforward route to a wide variety of substituted 2-aryl-1H-pyrroles from readily accessible starting materials. Iodoarenes bearing electron-withdrawing and electron-donating substituents are tolerated under the presented reaction conditions. The scope of the reaction is also expanded to N-aryl and -alkylpyrroles albeit in lower yields.

Facile synthesis of 2-arylpyrroles from 4-oxo-butanoic acids and their use in the preparation of bis(pyrrolyl)methanes

A range of 3-aroyl-propionic acids have been cyclised to unsaturated lactones which, upon reduction using DIBAL-H and reaction with an ammonia source, gave 2-arylpyrroles (Ar = Ph, 1-naphthyl, o-phenoxyphenyl and 4-methyl-2-methylsulfanylphenyl) in excellent yields. Reaction of 2,6-disubstituted aroylpropanals (Ar = 2,4,6-Me3C6H2, anthracenyl and 2-Me-naphthalen-1-yl) with an ammonia source failed to generate pyrroles. The arylpyrroles react readily with ketones or aldehydes in ethanol or under eutectic mix melt conditions to give bis-(pyrrolyl)methanes in excellent isolated yields.

Convenient access to 2-arylpyrroles from 2-lithio-N,N- dibenzylcyclopropylamine and nitriles

N,N-Dibenzylaminocyclopropyl ketimines formed as intermediates upon treatment of 2-lithiated N,N-dibenzylcyclopropylamines with nitriles, being donor-acceptor-substituted cyclopropanes, immediately underwent ring-enlarging rearrangement and 1,2-elimination of dibenzylamine to produce 2-substituted pyrroles in good yields (14 examples, 55-80%). Georg Thieme Verlag Stuttgart.

Ruthenium-catalyzed aromatization of enediynes via highly regioselective nucleophilic additions on a π-alkyne functionality. A useful method for the synthesis of functionalized benzene derivatives

TpRu(PPh3)(CH3CN)2PF6 (10 mol %) catalyst effected the nucleophilic addition of water, alcohols, aniline, acetylacetone, pyrroles, and dimethyl malonate to unfunctionalized enediynes under suitable conditions (100 °C, 12-24 h) and gave functionalized benzene products in good yields. In this novel cyclization, nucleophiles very regioselectively attack the internal C1′ alkyne carbon of enediynes to give benzene derivatives as a single regioisomer. Experiments with methoxy substituents exclude the possible involvement of naphthyl cations as reaction intermediates in the cyclization of (o-ethynylphenyl) alkynes. Deuterium-labeling experiments indicate that the catalytically active species is ruthenium-π-alkyne rather than ruthenium-vinylidene species. This hypothesis is further confirmed by the aromatization of o-(2′-iodoethynyl)phenyl alkynes with alcohols. We propose a nucleophilic addition/insertion mechanism for this nucleophilic aromatization on the basis of a series of experiments.

2-Bromo-N-(p-toluenesulfonyl)pyrrole: A Robust Derivative of 2-Bromopyrrole

2-Bromo-AL(p-toluenesulfonyl)pyrrole (2), a crystalline stable derivative of 2-bromopyrrole (1) has been prepared in 80% yield by bromination of pyrrole, followed by conversion to the N-(p-toluenesulfonyl) derivative. This compound is stable indefinitely at ambient temperature. Compound 2 is an excellent substrate for Suzuki coupling with arylboronic acids.

3,5-diaryl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes: Synthesis, spectroscopic, electrochemical, and structural properties

This research was undertaken to obtain new 'BODIPY' dyes that fluoresce at relatively long wavelengths. The title compounds 1a-e were prepared via a divergent route involving Suzuki couplings of arylboronic acids to N-tert- butoxycarbonyl-4-bromopyrrole 2, condensation of the products with an acid chloride, and incorporation of the boron difluoride entity. Two alkyl- substituted systems 7a and 7b were also prepared for comparison; the critical difference between structures 1 and 7 is that the former have an aryl group attached to each pyrrole nucleus whereas the latter only have alkyl substituents on that same ring. UV absorption and fluorescence emission data were compared for compounds 1 and 7. Absorption and fluorescence emission maxima for compounds 1 occur at higher wavelengths than for compounds 7, and the Stokes shifts for the aryl-substituted compounds 1 are larger than for the alkyl-substituted compounds 7. Fluorescence quantum yields measured for compounds 1 are less than for compounds 7, and possible reasons for this are outlined. Other physical data for the compounds were also collected. Oxidation and reduction potentials of the systems were obtained from cyclic voltammetry experiments, and a single-crystal X-ray structure determination was performed for the bisnaphthyl-substituted compound 1b.