19165-51-6

Upstream product

• 13667-12-4 1-bromo-4-phenylethynylbenzene 
• 15676-66-1 tri-n-butylindium 
• 79887-09-5 (4-butylphenyl)acetylene 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 20651-67-6 4-butyliodobenzene 
• 637-44-5 phenylpropyolic acid 
• 16635-23-7 phenyltriisopropoxytitanium(IV) 
• 147795-77-5 4-n-Butylphenyl-1-bromoacetylene 
• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 

Downstream Products

• 1174270-51-9 6-butyl-3-methyl-5-phenyl-2H-pyran-2-one 
• 1174270-40-6 5-butyl-3-methyl-6-phenyl-2H-pyran-2-one 

Relevant academic research and scientific papers

Effects of Multi-Carborane Substitution on the Photophysical and Electron-Accepting Properties of o-Carboranylbenzene Compounds

Multiple o-carborane substituted compounds, mono-, 1,3-bis-, and 1,3,5-tris[2-(4-butylphenyl)-o-carboran-1-yl]benzene (1–3), were prepared and characterized by multinuclear NMR spectroscopy and elemental analysis. The solid-state structures of 2 and 3 wer

Self-assembling behavior of binary mixture of hexa-peri-hexabenzocoronene derivatives with different molecular symmetry

The self-assembly and mesophase behavior of a series of mixtures of hexa-peri-hexabenzocoronene (HBC) derivatives carrying alkyl chains of different lengths at different positions and thus of different molecular symmetry (C1- and D3h-symmetry) were examined by powder X-ray diffractometry, UV–vis spectrometry, photoluminescence, polarizing optical microscopy, and differential scanning calorimetry. Significant reduction of isotropic phase transition temperature/clearing temperature was observed compare to single component symmetric analogues. The chain length modulates the mesophase behavior existed in the mixture. In particular, with long dodecyl groups, the mixture exhibited excimer/exciplex formation as well as aggregation induced emission phenomena in the non-polar solvent of hexane. Formation dynamics of intermolecular excimer/exciplex was studied by nuclear magnetic resonance and UV–vis spectroscopic method.

Highly efficient synthesis of 1,2-disubstituted acetylenes derivatives from the cross-coupling reactions of 1-bromoalkynes with organotitanium reagents

A Highly efficient route for the synthesis of 1,2-disubstituted acetylene derivatives has been developed by nickel catalyzed cross-couplings of alkynyl halides with aryl titanium reagents under mild conditions. This has given corresponding cross-coupling products good to excellent isolated yields of up to 92 %. The aryls bearing electron-donating or electron-withdrawing groups in either alkynylhalides or aryltitanium substrates gave cross-coupling products good yields. This process was simple and easily performed, which provides an efficient method for the synthesis of 1,2-disubstituted acetylenes derivatives.

Sonogashira Cross-Coupling of Aryltrimethylammonium Salts

A protocol for C(sp)-C(sp2) bond formation via the Sonogashira coupling reaction involving C-N bond cleavage with aryltrimethylammonium triflate as an electrophilic coupling partner is described in this work. The reactions proceeded well under mild conditions with a stoichiometric ratio of alkyl, aryl, or heteroaryl acetylenes and provided yields of up to 93%. Numerous useful functional groups were tolerated under the reaction conditions. Direct amine alkynylation can be achieved through a one-pot process without the isolation of ammonium salt. The protocol can be performed on a gram scale. Density functional theory calculations were performed to investigate the reaction mechanism that involved oxidative addition, alkyne coordination, deprotonation, and reductive elimination, which yielded the cross-coupling product.

Flow-based, cerium oxide enhanced, low-level palladium sonogashira and heck coupling reactions by perovskite catalysts

A flow chemistry procedure for Sonogashira and Heck cross-coupling reactions using a low-level palladium perovskite catalyst (LaFe 0.95Pd0.05O3) deposited on cerium oxide is reported. The catalyst was generated in situ at

Copper-catalyzed 2:1 Coupling reaction of arynes with alkynes

(Chemical Equation Presented) A formal insertion reaction of two molar amounts of arynes into a C-H bond of terminal alkynes is efficaciously catalyzed by copper(1) chloride, giving 2-alkynylbiaryls in one step.

Palladhim-catalyzed decarboxylative sp-sp2 cross-coupling reactions of aryl and vinyl halides and triflates with α,β-ynoic acids using silver oxide

Palladium-catalyzed decarboxylative sp-sp2 cross-coupling reactions of aryl and vinyl halides and triflates with α,β-ynoic acids using silver oxide have been developed. A variety of α,β-ynoic acids were readily decarboxylated in the presence of

New synthetic applications of indium organometallics in cross-coupling reactions

The use of indium organometallics in multifold and sequential cross-coupling reactions is reported. Triorganoindium reagents (R3In) react, under palladium catalysis, with oligohaloarenes affording the multiple cross-coupling products in a single operation. In the reaction, the three organic groups (alkyl, aryl, alkenyl or alkynyl) attached to indium are efficiently transferred to the electrophile, with only a slight excess of organometallic reagent. We demonstrate that indium organometallics are useful reagents for sequential cross-coupling reactions. This reaction illustrates the high chemoselectivity of R3In. Georg Thieme Verlag Stuttgart.