203176-36-7Relevant academic research and scientific papers
Nickel-Catalyzed, Regio- and Enantioselective Benzylic Alkenylation of Olefins with Alkenyl Bromide
Liu, Jiandong,Gong, Hegui,Zhu, Shaolin
supporting information, p. 4060 - 4064 (2020/12/25)
A NiH-catalyzed migratory hydroalkenylation reaction of olefins with alkenyl bromides has been developed, affording benzylic alkenylation products with high yields and excellent chemoselectivity. The mild conditions of the reaction preclude olefinic products from undergoing further isomerization or subsequent alkenylation. Catalytic enantioselective hydroalkenylation of styrenes was achieved by using a chiral bisoxazoline ligand.
Dual nickel- and photoredox-catalyzed reductive cross-coupling of aryl vinyl halides and unactivated tertiary alkyl bromides
Yu, Weijie,Chen, Long,Tao, Jiasi,Wang, Tao,Fu, Junkai
supporting information, p. 5918 - 5921 (2019/05/27)
A novel reductive cross-coupling of aryl vinyl halides and unactivated tertiary alkyl bromides has been realized via photoredox/nickel dual catalysis to produce vinyl arene derivatives bearing all-carbon quaternary centers with excellent E-selectivity. A stoichiometric metal reductant could be avoided by employing commercially available N,N,N′,N′-tetramethylethylenediamine (TMEDA) as the terminal reductant.
Construction of Phenanthrenes and Chrysenes from β-Bromovinylarenes via Aryne Diels-Alder Reaction/Aromatization
Singh, Vikram,Verma, Ram Subhawan,Khatana, Anil K.,Tiwari, Bhoopendra
supporting information, p. 14161 - 14167 (2019/10/28)
A highly efficient transition-metal-free general method for the synthesis of polycyclic aromatic hydrocarbons like phenanthrenes and chrysenes (and tetraphene) from β-bromovinylarenes and arynes has been developed. The reactions proceed via an aryne Diels-Alder (ADA) reaction, followed by a facile aromatization. This is the first report on direct construction of chrysenes (and tetraphene) using the ADA approach. Unlike the literature method which is limited to only 9/10-substituted derivatives, this method gives access to a wide variety of functionalized phenanthrenes.
cis-β-Bromostyrene derivatives from cinnamic acids via a tandem substitutive bromination-decarboxylation sequence
Tang, Khanh G.,Kent, Greggory T.,Erden, Ihsan,Wu, Weiming
, p. 3894 - 3896 (2017/09/15)
cis-β-Bromostyrene derivatives were synthesized stereospecifically from cinnamic acids through β-lactone intermediates. The synthetic sequence did not require the purification of the β-lactone intermediates although they were found to be stable and readily purified in most cases.
Ultrasonically Assisted Decarboxylative Bromination of α,β-Unsaturated Carboxylic Acids under Vilsmeier-Haack Conditions
Kumar, M. Satish,Rajanna,Venkanna,Venkateswarlu,Sudhakar Chary
, p. 642 - 646 (2015/12/26)
An efficient method for decarboxylative bromination of cinnamic acids (α,β-unsaturated carboxylic acids or 3-arylpropenoic acids) was achieved under relatively mild conditions using Vilsmeier-Haack reagent and KBr in acetonitrile media. Vilsmeier-Haack reagent is prepared by using 1:1 ratio of oxychloride (SOCl2 or POCl3) and DMF under chilled condition. Ultrasonically assisted reactions underwent smoothly with highly significant rate enhancements and afforded bromostyrenes as products in very good yields even though the reactions were too sluggish.
Preparation of Vinyl Arenes by Nickel-Catalyzed Reductive Coupling of Aryl Halides with Vinyl Bromides
Liu, Jiandong,Ren, Qinghua,Zhang, Xinghua,Gong, Hegui
supporting information, p. 15544 - 15548 (2016/12/09)
This work emphasizes the synthesis of substituted vinyl arenes by reductive coupling of aryl halides with vinyl bromides under mild and easy-to-operate nickel-catalyzed reaction conditions. A broad range of aryl halides, including heteroaromatics, and vinyl bromides were employed to yielding products in moderate to excellent yields with high functional-group tolerance. The nickel-catalytic system displays good chemoselectivity between the two C(sp2)-halide coupling partners, thus demonstrating a mechanistic pathway distinct from other stepwise protocols.
Palladium(0)-catalyzed cross-coupling of 1,1-diboronates with vinyl bromides and 1,1-dibromoalkenes
Li, Huan,Zhang, Zhikun,Shangguan, Xianghang,Huang, Shan,Chen, Jun,Zhang, Yan,Wang, Jianbo
supporting information, p. 11921 - 11925 (2015/01/09)
Palladium-catalyzed cross-coupling reactions of 1,1-diboronates with vinyl bromides and dibromoalkenes were found to afford 1,4-dienes and allenes, respectively. These reactions utilize the high reactivities of both 1,1-diboronates and allylboron intermediates generated in the initial coupling.
Novel system for decarboxylative bromination of α,β-unsaturated carboxylic acids with diacetoxyiodobenzene
Fursule, Ravindra Abhykumar,Patil, Pravin Onkar,Shewale, Bharti Devaji,Kosalge, Satish Bhaskar,Deshmukh, Prashant Krishnarao,Patil, Dilip Ashok
experimental part, p. 1243 - 1245 (2010/08/06)
A simple and mild method for the conversion of varieties of α,β-unsaturated carboxylic acids to the corresponding bromoalkenes using diacetoxyiodobenzene (IBD) in combination with tetraethyl-ammonium bromide (TEAB) at room temperature is discussed. Advantages of this system are short reaction time, easy work up and gave good to excellent yields.
A mild procedure for the stereospecific transformation of trans cinnamic acid derivatives to cis β-bromostyrenes
Kim, Sun Hee,Wei, Han-Xun,Willis, Steven,Li, Guigen
, p. 4179 - 4185 (2007/10/03)
A new mild procedure has been developed for the synthesis of cis β- bromostyrene analogs with complete Z/E selectivity and good to excellent yields (58.4 - 90.9 %). The process involves carboxyl-halo-elimination of cinnamic acid dibromides by using triethylamine in N,N-dimethylformamide at room temperature. A one-pot procedure has also been described for the direct transformation of cinnamic acids to β-bromostyrenes.
