356759-39-2

Upstream product

• 253684-21-8 1,1-dibromo-2-(4-methoxycarbonylphenyl)ethene 
• 1571-08-0 methyl 4-formylbenzoate 
• 3034-86-4 4-ethynylbenzoic acid methyl ester 
• 117390-07-5 (E)-4-(methoxycarbonyl)cinnamic acid 

Downstream Products

• 1616973-22-8 methyl 4-{1-[(4-methylphenyl)sulfonyl]-1H-1,2,3-triazol-4-yl}benzoate 
• 3034-86-4 4-ethynylbenzoic acid methyl ester 

Relevant academic research and scientific papers

Regio- and stereoselective synthesis of bromoalkenes by homolytic hydrobromination of alkynes with hydrogen bromide

Homolytic hydrobromination of terminal and internal alkynes with a commercially available solution of hydrogen bromide in acetic acid has been investigated for regio- and stereoselective synthesis of bromoalkenes. Under an aerobic atmosphere at room temperature, the reaction of ethynylarenes with a small excess of HBr efficiently gave (2-bromoethenyl)arenes with good to high E-selectivity. (Alk-1-ynyl)arenes, or internal alkynes bearing both phenyl and alkyl groups at the sp-carbons also underwent the air-initiated hydrobromination to exhibit high Z-selectivity under kinetic conditions using a half equivalent of HBr.

The hydrodebromination of 1,1-dibromoalkenes via visible light catalysis

Vinyl bromides are versatile synthetic intermediates and widely applied in organic synthesis and pharmaceuticals. Herein, a hydrodebromination reaction of 1,1-dibromoalkenes was established via visible light catalysis. A variety of structurally different vinyl bromides were obtained in moderate to excellent yields.

Ohmic Heating and Ionic Liquids in Combination for the Indium-Promoted Synthesis of 1-Halo Alkenyl Compounds: Applications to Pd-Catalysed Cross-Coupling Reactions

We have explored the combination of ohmic heating (ΩH) with ionic liquids for indium-promoted reactions and report herein the indium-promoted dehalogenation of gem-dibromo alkenes and the indium-mediated reductive elimination of chlorohydrins for the synthesis of 1-halo alkenyl derivatives. Heck, Stille, Suzuki, Kumada and Sonogashira couplings of the resulting 1-halo-1-alkenes with appropriate reagents were carried out to give alkenes, dienes and enynes. We report herein the combination of ohmic heating (ΩH) with ionic liquids for the indium-promoted dehalogenation of gem-dibromo alkenes and the indium-mediated reductive elimination of chlorohydrins. The 1-halo alkenyl derivatives synthesized were then submitted to a series of cross-coupling reactions to give conjugated alkenes, dienes and enynes.

Stereoselective synthesis of (Z)-β-arylvinyl bromides from anti-2,3-dibromo-3-arylpropanoic acids

A novel method for the stereoselective synthesis of (Z)-β-arylvinyl bromides in excellent yields by debrominative decarboxylation of anti-2,3-dibromo-3-arylpropanoic acids using NaN3 was developed. This facile transformation was achieved under room temperature for 1-2 h.

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 (Z)-1-bromo-1-alkenes and terminal alkynes from anti-2,3-dibromoalkanoic acids by microwave-induced reaction

(Z)-1-Bromo-1-alkenes were stereoselectively prepared in high yields in a short reaction time by microwave irradiation of the corresponding anti-2,3-dibromoalkanoic acids in a Et3N/DMF system. A one-pot synthesis of terminal alkynes and enynes from 2,3-dibromoalkanoic acids were also developed by microwave-induced reaction.

A one-pot synthesis of terminal alkynes from anti-3-aryl-2,3- dibromopropanoic acids under microwave irradiation

A facile one-pot synthesis of terminal alkynes was achieved by microwave irradiation of a mixture of anti-3-aryl-2,3-dibromopropanoic acids, Et 3N and DMF and subsequent irradiation in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). This method requires short reaction time (1-2 min) and gives terminal alkynes in high yields. Copyright

Stereoselective synthesis of (E)-β-arylvinyl bromides by microwave-induced reaction of anti-3-aryl-2,3-dibromopropanoic acids using an AgOAc-AcOH system

(E)-β-Arylvinyl bromides were stereoselectively prepared in high yields by microwave irradiation of the corresponding anti-3-aryl-2,3- dibromopropanoic acids in AcOH in the presence of AgOAc for 0.5-3.0 min. (E)-β-Arylvinyl bromides were stereoselectively prepared in high yields by microwave irradiation of the corresponding anti-3-aryl-2,3-dibromo-propanoic acids in AcOH in the presence of AgOAc for 0.5-3.0 min.

Convenient and stereoselective synthesis of (Z)-1-bromo-1-alkenes by microwave-induced reaction

(Z)-1-Bromo-1-alkenes were stereoselectively prepared in high yields in a short reaction time (0.2-1.0 min) by microwave irradiation of the corresponding 2,3-dibromoalkanoic acids in DMF in the presence of triethylamine.