18462-35-6Relevant academic research and scientific papers
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.
Synthesis of Substituted Quinolizidines via a Gold-Catalyzed Double Cyclization Cascade
Nonaka, Shiori,Sugimoto, Kenji,Ueda, Hirofumi,Tokuyama, Hidetoshi
, p. 380 - 385 (2016/02/12)
A novel synthesis of quinolizidines by a cationic gold-catalyzed double cyclization cascade has been developed. The reaction was initiated by the gold-catalyzed 6-exo-dig cyclization of ynamides, which was followed by a second cyclization of an enamide intermediate to provide the corresponding quinolizidine derivatives. The utility of this reaction was demonstrated by application to the synthesis of multi-substituted quinolizidines and by the total synthesis of a quinolizidine alkaloid, (±)-lupinine.
A Convenient Stereoselective Reduction of Gem-Dibromides with a Combination of Dimethyl Phosphite and Potassium Carbonate
Zhao, Yalei,Chen, Tieqiao,Wang, Xiang-Bo,Han, Li-Biao
, p. 1820 - 1827 (2015/12/12)
An efficient and highly stereoselective reduction of a gem-dibromocyclopropane to the corresponding monobromocyclopropane under mild reaction conditions was developed using a combination of dimethyl phosphite and potassium carbonate. This reaction provided a simple and practical way for the synthesis of the valuable monobromocyclopropanes and β-monobromoalkenes.
Pd-Catalyzed Difluoromethylation of Vinyl Bromides, Triflates, Tosylates, and Nonaflates
Chang, Dalu,Gu, Yang,Shen, Qilong
supporting information, p. 6074 - 6078 (2015/04/14)
Pd-catalyzed difluoromethylation of di-, tri- or tetra-substituted vinyl bromides, triflates, tosylates and nonaflates under mild conditions is described. The reaction tolerates a wide range of functional groups, such as bromide, chloride, fluoride, ester, amine, nitrile, and protected carbonyl, thus providing a general route for the preparation of difluoromethylated alkenes. Vinyl fantasy: Pd-catalyzed difluoromethylation of di-, tri-, or tetra-substituted vinyl bromides, triflates, tosylates, and nonaflates under mild conditions is described. The reaction tolerates a wide range of functional groups, such as bromide, chloride, fluoride, ester, amine, nitrile, and protected carbonyl, thus providing a general route for the preparation of difluoromethylated alkenes.
Nucleophile-selective cross-coupling reactions with vinyl and alkynyl bromides on a dinucleophilic aromatic substrate
He, Lu-Ying,Schulz-Senft, Mathias,Thiedemann, Birk,Linshoeft, Julian,Gates, Paul J.,Staubitz, Anne
supporting information, p. 2498 - 2502 (2015/04/22)
A nucleophile-selective cross-coupling reaction on an aromatic compound bearing two metal groups, Bpin and SnMe3, has been developed. Previously, only aryl bromides and iodides could be used as electrophilic components, but in this work, the scope could be extended to vinyl and alkynyl bromides as electrophiles. This means that the roles typical in Sonogashira couplings or Heck reactions of the aromatic ring as the dielectrophile coupling to vinyl and alkynyl metal species are reversed, which presents a new tool for organic synthesis. The first nucleophilic site to react is the stannyl group, and subsequently, a Suzuki-Miyaura cross-coupling reaction can take place on the same molecule.
H-β-zeolite catalyzed synthesis of β-bromostyrenes from styrene bromohydrins
Pappula, Venkatanarayana,Donthiri, Ramachandra Reddy,Darapaneni, Chandra Mohan,Subbarayappa, Adimurthy
supporting information, p. 1793 - 1795 (2014/03/21)
Synthesis of β-bromostyrenes from styrene bromohydrins using H-β-zeolite as catalyst under moderate conditions is reported. The catalyst could be regenerated and reused up to three consecutive cycles.
A novel method for bromodecarboxylation of α,β-unsaturated carboxylic acids using catalytic sodium nitrite
Telvekar, Vikas N.,Takale, Balaram S.
experimental part, p. 2394 - 2396 (2011/05/09)
A first novel synthetic utility of catalytic sodium nitrite in combination with aqueous HBr, for bromo decarboxylation of α,β-unsaturated carboxylic acid is described. α,β-Unsaturated carboxylic acid compounds successfully converted into corresponding bromo compounds. The advantages of this protocol are shorter reaction time and moderate to good yields.
A novel system for decarboxylative bromination
Telvekar, Vikas N.,Chettiar, Somsundaram N.
, p. 4529 - 4532 (2008/02/03)
A simple and mild method for decarboxylative bromination of α,β-unsaturated carboxylic acids has been developed using diphosphorus tetraiodide in combination with tetraethylammonium bromide (TEAB) at room temperature. High yields of the corresponding bromoalkenes were obtained.
Mild and efficient method for decarboxylative bromination of α,β-unsaturated carboxylic acids with Dess-Martin periodinane
Telvekar, Vikas N.,Arote, Nitin D.,Herlekar, Omkar P.
, p. 2495 - 2497 (2007/10/03)
A simple and mild method for decarboxylative bromination of α,β-unsaturated carboxylic acids has been developed using Dess-Martin Periodinane (DMP) in combination with tetraethylammonium bromide (TEAB) at room temperature. High yields of the corresponding bromoalkenes were obtained. Georg Thieme Verlag Stuttgart.
Halodecarboxylation of a,β-unsaturated carboxylic acids bearing aryl and styrenyl group at β-carbon with Oxone and sodium halide
You,Lee
, p. 105 - 107 (2007/10/03)
Reaction of α,β-unsaturated carboxylic acid bearing aryl and styrenyl group at β-carbon with Oxone and sodium halide in aqueous acetonitrile afforded the corresponding haloalkenes.
