80350-66-9

Upstream product

• 90766-67-9 1-(4,4-dibromobuta-1,3-dien-1-yl)benzene 
• 762-04-9 phosphonic acid diethyl ester 
• 90766-67-9 1,1-dibromo-4-phenyl-1,3-butadiene 
• 14371-10-9 (E)-3-phenylpropenal 
• 39598-55-5 (bromomethylene)triphenylphosphorane 
• 104-55-2 3-phenyl-propenal 

Downstream Products

• 1206103-28-7 (1E,3E,5E)-1-(4-hydroxy-3-methoxyphenyl)-6-phenyl-1,3,5-hexatriene 
• 1206103-29-8 (1E,3E,5E)-1-(4-hydroxy-3,5-dimethoxyphenyl)-6-phenyl-1,3,5-hexatriene 
• 682756-54-3 (1E,3E,5E)-1-(4-hydroxyphenyl)-6-phenyl-1,3,5-hexatriene 
• 1402435-18-0 3-((1E, 3E)-4-phenylbuta-1,3-dien-1-yl)cyclohex-2-en-1-one 
• 1402434-87-0 (S)-3-ethyl-3-((1E,3E)-4-phenylbuta-1,3-dien-1-yl)cyclohexanone 
• 36892-91-8 diethyl 4-phenylbutadienephosphonate 
• 261632-75-1 1,2,3,4-tetraphenyl-6-(2-phenylethenyl)fulvene 
• 1059590-39-4 butyl (2E,4E,6E,8E)-4,5,9-triphenyl-2,4,6,8-nonatetraenoate 
• 89510-60-1 all-trans-1--4-phenyl-1,3-butadiene 
• 188802-38-2 ((1E,3E)-4-bromobuta-1,3-dienyl)benzene 
• 2096-81-3 C₂₂H₁₉OP 
• 1429762-95-7 C₃₄H₃₀O₂P₂ 
• 32174-26-8 (E)-9-(3-phenylallylidene)-9H-fluorene 

Relevant academic research and scientific papers

Ni-catalyzed reductive coupling of α-halocarbonyl derivatives with vinyl bromides

This work describes the vinylation of α-halo carbonyl compounds with vinyl bromides under Ni-catalyzed reductive coupling conditions. While aryl-conjugated vinyl bromides entail pyridine as the sole labile ligand, the alkyl-substituted vinyl bromides require both bipyridine and pyridine as the co-ligands.

Metal-Mediated Debromination of gem-Dibromoalkenes under Mild Conditions

We describe the facile and efficient metal-promoted reduction of C-Br bonds of gem-dibromides. When the reaction is mediated by indium, the corresponding vinyl bromides are obtained in good yields and high E-stereoselectivities. Alternatively, when the reduction is mediated by samarium diiodide, vinyl bromides are obtained in moderate yields and good Z-selectivities.

Tellurium-promoted stereoselective hydrodebromination of 1,1-dibromoalkenes: Synthesis of (: E)-bromoalkenes

We describe herein an efficient and simple method for the stereoselective hydrodebromination of 1,1-dibromoalkenes by using a catalytic amount of the nucleophilic species of tellurium, generated in situ by the reaction of elemental tellurium with NaBH4. By this methodology, (E)-bromoalkenes were obtained in moderate to excellent yields under mild reaction conditions, without the use of transition metals or base. Furthermore, a high stereoselectivity for the (E)-isomer was observed when 1,1-dibromoarylalkenes were used, thus indicating a promising alternative for future applications in organic synthesis.

Preparation of Vinyl Arenes by Nickel-Catalyzed Reductive Coupling of Aryl Halides with Vinyl Bromides

This work emphasizes the synthesis of substituted vinyl arenes by reductive coupling of aryl halides with vinyl bromides under mild and easy-to-operate nickel-catalyzed reaction conditions. A broad range of aryl halides, including heteroaromatics, and vinyl bromides were employed to yielding products in moderate to excellent yields with high functional-group tolerance. The nickel-catalytic system displays good chemoselectivity between the two C(sp2)-halide coupling partners, thus demonstrating a mechanistic pathway distinct from other stepwise protocols.

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

Formation of quaternary stereogenic centers by NHC-Cu-catalyzed asymmetric conjugate addition reactions with Grignard reagents on polyconjugated cyclic enones

The copper-catalyzed conjugate addition of various Grignard reagents to polyconjugated enones (dienone and enynone derivatives) is reported. The catalyst system, composed of copper triflate and an NHC ligand, led to the unusual selective formation of the 1,4-addition products. This reaction allows for the creation of all-carbon chiral quaternary centers with enantiomeric excesses up to 99 %. The remaining unsaturation on the 1,4 adducts give access to valuable synthetic transformations. Copyright

PALLADIUM-CATALYZED NEW CARBON-PHOSPHORUS BOND FORMATION

Dialkyl arylphosphonates are prepared by the palladium-catalyzed reaction of aryl bromides with dialkyl phosphite in the presence of triethylamine.The similar treatment of vinyl bromides gives dialkyl vinylphosphonates stereoselectively.

A convenient synthesis of 1-bromoolefins and acetylenes by a chain extension of aldehydes

Aldehydes are easily converted to 1-bromoolefins or terminal acetylenes by the use of Wittig reaction of bromomethylenetriphenylphosphorane which is prepared from bromomethyltriphenylphosphonium bromide with potassium tert-butoxide.