77295-67-1

Upstream product

• 558-13-4 carbon tetrabromide 
• 623-27-8 terephthalaldehyde, 
• 603-35-0 triphenylphosphine 
• 589-29-7 p-xylylene glycol 
• 56506-90-2 (dibromomethyl)(triphenyl)phosphonium bromide 
• 36603-99-3 terephthalic aldehyde dihydrazone 
• 624-38-4 para-diiodobenzene 

Downstream Products

• 360549-86-6 1,4-bis[4-trimethylsilyl-2-(trimethylsilylethynyl)but-1-en-3-ynyl]benzene 
• 131941-37-2 1,4-bis[(4-fluorophenyl)ethynyl]benzene 
• 1849-27-0 1,4-bis(2-phenylethynyl)benzene 
• 64984-68-5 (E,E)-1,4-bis(β-bromovinyl)benzene 
• 4843-45-2 3,3′-(1,4-phenylene)dipropiolic acid 
• 935-14-8 1,4-diethynylbenzene 
• 65127-72-2 1,4-bis-(2-bromoethynyl)benzene 
• 7325-46-4 1,4-phenylenediacetic acid 
• 133942-93-5 1,4-bis(1,1-diphenyl-2-ethenyl)benzene 
• 1262966-32-4 tetraisopropyl ((1E,1'E)-1,4-phenylenebis(ethene-2,1-diyl))bis(phosphonate) 

Relevant academic research and scientific papers

Synthesis of bis(halovinyl)benzenes by catalytic olefination

Catalytic olefination of hydrazines of terephthalic and isophthalic aldehydes with polyhaloalkanes afforded the corresponding p- and m-divinylbenzene derivatives bearing halogen atoms and various functional groups at the double bonds. Stereochemical featu

Nickel(II)-magnesium-catalyzed cross-coupling of 1,1-dibromo-1-alkenes with diphenylphosphine oxide: One-pot synthesis of (E)-1-alkenylphosphine oxides or bisphosphine oxides

A novel nickel(II)-magnesium-mediated cross-coupling of diphenylphosphine oxide with a variety of 1,1-dibromo-1-alkenes has been developed, which provides a powerful and general methodology for the stereoselective synthesis of various (E)-1-alkenylphosphine oxides or bisphosphine oxides, with operational simplicity of the procedure, good to high yields and broad substrate applicability. Mechanistic studies reveal that the reaction might involve a Hirao reduction, cross-coupling and Michael addition. Copyright

Synthesis of dibromoolefins via a tandem ozonolysis-dibromoolefination reaction

In this Letter we outline the synthesis of a variety of dibromoolefins (DBOs) from a series of alkenes by coupling an oxidative cleavage and a reaction with a phosphorous ylide. This approach strategically avoids isolation of reactive aldehyde intermediates and presents one of the few examples coupling carbon-carbon bond formation with ozonolysis.

Cycloaddition-based formal C-H alkynylation of isoindoles leading to the synthesis of air-stable fluorescent 1,3-dialkynylisoindoles

Reaction of N-alkylisoindoles with (bromoethynyl)triisopropylsilane afforded 1,3-bis(triisopropylsilylethynyl) isoindoles in high yields. The formal C-H alkynylation proceeds under transition-metal-free conditions through [4 + 2] cycloaddition of the pyrrole ring of isoindole with bromoalkyne followed by ring-opening of the product.

Pd-catalyzed domino synthesis of internal alkynes using triarylbismuths as multicoupling organometallic nucleophiles

Figure presented The domino coupling reaction of 1,1-dibromo-1-alkenes with triarylbismuth nucleophiles has been demonstrated to furnish disubstituted alkynes directly under catalytic palladium conditions. The couplings of triarylbismuths as multicoupling nucleophiles with 3 equiv of 1,1-dibromo-1-alkenes are very fast, affording high yields of alkynes in a short reaction time. Thus, an efficient domino process has been accomplished using 1,1-dibromo-1-alkenes as surrogates for internal alkyne synthesis in couplings with triarylbismuths in a one-pot operation.

A new facile synthesis of 1,1-dibromo-2-arylethenes

Synthetically useful 1,1-dibromo-2-arylethenes were readily prepared in good yields via double bromodesilylation of the easily accessible 1,1-bis(trimethylsilyl)-2-arylethenes using N-bromosuccinimide under mild conditions. Georg Thieme Verlag Stuttgart.

Tetraarylphosphonium salts as solubility-control groups: Phosphonium-supported triphenylphosphine and azodicarboxylate reagents

(Chemical Equation Presented) Predictable solubilities! Reagents supported on a tetraarylphosphonium group have solubilities that can be predicted. The reagents and their by-products can be readily removed, recovered, and recycled after reaction by a precipitation/filtration sequence initiated by the addition of a low-polarity solvent, such as diethyl ether. Furthermore, the supported reagents are robust and exhibit reactivities similar to their parent compounds.

One-pot conversion of activated alcohols into 1,1-dibromoalkenes and terminal alkynes using tandem oxidation processes with manganese dioxide

Approaches to the preparation of C1-homologated dibromoalkenes and terminal alkynes from activated alcohols using one-pot tandem oxidation processes (TOPs) with manganese dioxide are outlined. The conversion of alcohols into dibromoalkenes is described using dibromomethyltriphenylphosphonium bromide and the formation of terminal alkynes was achieved via a sequential one-pot, two-step process utilising the Bestmann-Ohira reagent.

A tandem oxidation procedure for the conversion of alcohols into 1,1-dibromoalkenes

A practical and concise route to dibromoalkenes directly from activated alcohols in good to excellent yields using a new Tandem Oxidation Procedure (TOP) is reported. We also describe the use of these dibromoalkenes as intermediates in a one-pot route to 4,5-dihydro-1H-imidazoles and in the synthesis of bromoalkynes through MTBD-induced elimination.

Synthesis and photophysical studies of bis-enediynes as tunable fluorophores

We have synthesized a family of bis-enediynes by two complementary Pd/Cu-catalyzed Sonogashira cross-coupling methods. One is a modified Sonogashira reaction between the TMS-protected tetraalkyne 20 (or 21) and various aromatic bromides to afford bis-enediynes 22a-d and 23a-d bearing different peripheral aryl units. The other, the reaction of bifunctional 1,1-dibromo-1-alkenes with phenylacetylene, afforded a series of bis-enediynes 24-32 bearing various core aryl groups. These chemical modifications to the core and periphery of bis-enediynes induce dramatic changes in absorption and emission spectra. Bis-enediynes 22 and 23 show a large Stokes shift of about 50-110 nm when compared to the less-conjugated bis-enediynes 20 and 21. Absorptions and emissions of bis-enediynes 25, 27-29, and 31 were red-shifted relative to those of enediyne 35. Substantial increases in fluorescence quantum yields are observed as a result of extending the π-conjugation. The emission wavelength of bis-enediynes was tailored from indigo blue to reddish-orange, suggesting that the color of emission can be tunable by modification of the core and/or peripheral units.