125428-11-7Relevant articles and documents
Engaging Alkenyl Halides with Alkylsilicates via Photoredox Dual Catalysis
Patel, Niki R.,Kelly, Christopher B.,Jouffroy, Matthieu,Molander, Gary A.
, p. 764 - 767 (2016)
Single-electron transmetalation via photoredox/nickel dual catalysis provides the opportunity for the construction of Csp3-Csp2 bonds through the transfer of alkyl radicals under very mild reaction conditions. A general procedure for the cross-coupling of primary and secondary (bis-catecholato)alkylsilicates with alkenyl halides is presented. The developed method allows not only alkenyl bromides and iodides but also previously underexplored alkenyl chlorides to be employed. (Chemical Equation Presented).
A green Hunsdiecker reaction: Synthesis of β-bromostyrenes from the reaction of α,β-unsaturated aromatic carboxylic acids with KBr and H2O2 catalysed by Na2MoO4·2H2O in aqueous medium
Sinha,Layek,Mandal,Bhattacharjee
, p. 1916 - 1917 (2001)
Reaction of α,β-unsaturated aromatic carboxylic acids with KBr and H2O2 in the presence of Na2MoO4·2H2O in aqueous medium affords β-bromo alkenes in high yield.
Regio- and stereoselective synthesis of bromoalkenes by homolytic hydrobromination of alkynes with hydrogen bromide
Kinoshita, Hidenori,Kumaki, Wataru,Miura, Katsukiyo
, (2022/03/07)
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.
Cyclic Diaryl λ3-Bromanes: A Rapid Access to Molecular Complexity via Cycloaddition Reactions
Lanzi, Matteo,Ali Abdine, Racha Abed,De Abreu, Maxime,Wencel-Delord, Joanna
supporting information, p. 9047 - 9052 (2021/12/06)
Biaryls have widespread applications in organic synthesis. However, sequentially polysubstituted biaryls are underdeveloped due to their challenging preparation. Herein, we report the synthesis of dissymetric 2,3,2′,3′,4-substituted biaryls via pericyclic reactions of cyclic diaryl λ3-bromanes. The functional groups tolerance and atom economy allow access to molecular complexity in a single reaction step. Continuous flow protocol has been designed for the scale-up of the reaction, while postfunctionalizations have been developed taking advantage of the residual Br-atom.
The hydrodebromination of 1,1-dibromoalkenes via visible light catalysis
Sun, Wencheng,Teng, Qiaoling,Cheng, Dongping,Li, Xiaonian,Xu, Xiaoliang
supporting information, (2019/12/05)
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.
