131428-24-5Relevant articles and documents
Iron-Catalyzed Regioselective Alkenylboration of Olefins
Yu, Xiaolong,Zheng, Hongling,Zhao, Haonan,Lee, Boon Chong,Koh, Ming Joo
supporting information, p. 2104 - 2109 (2020/11/30)
The first examples of an iron-catalyzed three-component synthesis of homoallylic boronates from regioselective union of bis(pinacolato)diboron, an alkenyl halide (bromide, chloride or fluoride), and an olefin are disclosed. Products that bear tertiary or quaternary carbon centers could be generated in up to 87 % yield as single regioisomers with complete retention of the olefin stereochemistry. With cyclopropylidene-containing substrates, ring cleavage leading to trisubstituted E-alkenylboronates were selectively obtained. Mechanistic studies revealed reaction attributes that are distinct from previously reported alkene carboboration pathways.
The hydrodebromination of 1,1-dibromoalkenes via visible light catalysis
Sun, Wencheng,Teng, Qiaoling,Cheng, Dongping,Li, Xiaonian,Xu, Xiaoliang
, (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.
TsNBr2 promoted decarboxylative bromination of α,β-unsaturated carboxylic acids
Hazarika, Debojit,Phukan, Prodeep
supporting information, p. 4593 - 4596 (2018/11/23)
A rapid process for decarboxylative bromination of α,β-unsaturated carboxylic acids have been developed using N,N-dibromo-p-toluenesulfonamide (TsNBr2). Treatment of cinnamic acids with TsNBr2 in presence of potassium carbonate in acetonitrile produces corresponding β-bromostyrenes at room temperature. Exclusive formation of (E)-β-bromostyrenes was observed in a stereoselective manner within a very short period of time (5–15 min). This method was further extended for obtaining 1-bromoalkynes from corresponding propiolic acids. Instantaneous formation of bromoalkynes was observed when the reaction was carried out in presence of DBU as a base in acetonitrile at room temperature. A wide variety of cinnamic acids and propiolic acids could be converted to corresponding β-bromostyrenes and 1-bromoalkynes respectively under mild reaction condition with high to excellent yield.