77150-90-4

Upstream product

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

Downstream Products

• 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 
• 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 

Relevant academic research and scientific papers

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.

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.

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

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.