21979-82-8Relevant academic research and scientific papers
Tetrabromobutatriene: Completing the perhalocumulene series
Liu, Pei-Hua,Li, Lei,Webb, Jeffrey A.,Zhang, Yi,Goroff, Nancy S.
, p. 2081 - 2083 (2004)
Tetrabromobutatriene, C4Br4, can be prepared directly from dibromobutadiyne by reaction with Br2 at -25°C in concentrated hexanes solution. The cumulene precipitates out of the reaction mixture as a yellow powder. Under palladium-catalyzed coupling conditions, C4Br4 can undergo allylic rearrangement, giving a mixture of products, including some with butenyne backbones. However, in furan solution, C4Br4 reacts cleanly at its central double bond to give the furan Diels-Alder adduct. Under Suzuki conditions, this adduct reacts at the furan double bond rather than at bromide.
Metal-Free Electrophilic Phosphination/Cyclization of Alkynes
Unoh, Yuto,Hirano, Koji,Miura, Masahiro
supporting information, p. 6106 - 6109 (2017/05/09)
A metal-free electrophilic phosphination reaction has been developed. Electrophilic phosphorus species generated in situ from secondary phosphine oxides and Tf2O smoothly couple with alkynes possessing pendant nucleophiles to afford the corresponding phosphinated cyclization products in good yield. Preliminary NMR studies show that phosphirenium species may be involved as intermediates of the cyclization reactions.
Palladium- and nickel-catalyzed kumada cross-coupling reactions of gem -difluoroalkenes and monofluoroalkenes with Grignard reagents
Dai, Wenpeng,Xiao, Juan,Jin, Guanyi,Wu, Jingjing,Cao, Song
, p. 10537 - 10546 (2015/02/19)
A novel Kumada-Tamao-Corriu cross-coupling reaction of gem-di- or monofluoroalkenes with Grignard reagents, with or without β-hydrogen atoms, in the presence of a catalytic amount of palladium- or nickel-based catalysts has been developed. The reaction is performed under mild conditions (room temperature or reflux in diethyl ether for 1-2 h) and leads to di-cross- or mono-cross-coupled products in good to high yields.
Synthesis of polysubstituted enynes through iron-catalyzed carbomagnesiation of conjugated diynes
Ilies, Laurean,Yoshida, Takumi,Nakamura, Eiichi
supporting information, p. 527 - 530 (2014/03/21)
Symmetrical and unsymmetrical conjugated diynes are chemo-, regio-, and stereoselectively carbomagnesiated with a ?Grignard reagent at room temperature in the presence of a catalytic amount of FeCl2 without the need for an external ligand. The resulting magnesium intermediate can be further functionalized to give polysubstituted 1,3-enyne derivatives. Georg Thieme Verlag Stuttgart New York.
A single-step synthesis of enynes: Pd-catalyzed arylalkynylation of aryl iodides, internal alkynes, and alkynylsilanes
Sakai, Norio,Komatsu, Ryosuke,Uchida, Naoki,Ikeda, Reiko,Konakahara, Takeo
supporting information; experimental part, p. 1300 - 1303 (2010/06/15)
"Chemical Equation Presented" An unprecedented single-step synthesis of enyne derivatives through Pd-catalyzed arylalkynylation of aryl iodides, internal alkynes, and alkynylsilanes is described.
Efficient synthesis of enynes by tetraphosphine-palladium-catalysed reaction of vinyl bromides with terminal alkynes
Feuerstein, Marie,Chahen, Ludovic,Doucet, Henri,Santelli, Maurice
, p. 112 - 120 (2007/10/03)
Through the use of [PdCl(C3H5)]2/cis,cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane as catalyst, a range of vinyl bromides undergoes Sonogashira cross-coupling reaction with a variety of alkynes, leading to
Vinyl Cations in Organic Synthesis. Part 2. A Novel Synthesis of Methylene-1H-indenes (Benzofulvenes) by Cyclisation of Phenyl-substituted But-1-en-3-ynes
Marcuzzi, Franco,Azzena, Ugo,Melloni, Giovanni
, p. 2957 - 2960 (2007/10/02)
A series of phenyl-substituted but-1-en-3-ynes has been prepared and their reactivity toward acid-catalysed cycloisomerisation investigated.In boiling dichloromethane of 1,2-dibromoethane in the presence of a catalytic amount of methanesulfonic acid, 1,1,
