25108-56-9Relevant academic research and scientific papers
Cobalt-catalyzed vinylation of functionalized aryl halides with vinyl acetates
Amatore, Muriel,Gosmini, Corinne,Perichon, Jacques
, p. 989 - 992 (2005)
A new method for the preparation of styrene derivatives is described on the basis of the activation of aryl halides by low-valent cobalt species. A combination of CoII bromide and 2,2′-bipyridine is suitable as catalyst for the cross-coupling reaction of a wide range of aromatic halides (X = Cl, Br, I), mostly bearing sensitive moieties, with vinyl acetates. These reactions proceed under mild conditions in the presence of the appropriate reducing agent to afford α-substituted styrene compounds in satisfactory to high yields. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
Sequential olefination-dimerisation of benzylic dithioacetals by the nickel-catalysed reaction with methyl Grignard or zinc reagent
Lai, Guo-Qiao,Li, Ze,Luh, Tien-Yau,Yu, Lei,Zhang, Pinglu
, p. 9653 - 9659 (2022/05/02)
Products of main group elements from cross-coupling reactions have been shown to serve as Lewis acids, mediating further reactions of organic coupling products. Thus, the nickel-catalysed olefination of benzylic dithioacetal with MeMgI in benzene in a sealed Schlenk tube at 130 °C generates magnesium mercaptide which regioselectively converts 2-arylpropene into a dimer in good yield. Aryl iodide reacts with 2-propenylmagnesium bromide in the presence of 1,2-ethanedithiol and NiCl2(PPh3)2 to yield the same dimer. Replacement of the Grignard reagent by an organozinc reagent gives the dimers in a better yield.
Selective Synthesis of Substituted Pyridines and Pyrimidines through Cascade Annulation of Isopropene Derivatives
Chen, Lu,He, Runfa,Huang, Yubing,Li, Jiaming,Li, Jian,Li, Yibiao,Liu, Jiasheng,Liu, Yang
supporting information, p. 1620 - 1625 (2022/03/14)
Diverse substituted pyridines and pyrimidines with high selectivity were obtained using a concise and efficient protocol developed herein. The reaction proceeds via metal-free cascade annulation of isopropene derivatives. Using isopropene derivatives as C3 synthons, NH4I as the “N” source, and formaldehyde or dimethyl sulfoxide as the carbon source, this reaction realizes the efficient formation of intermolecular C-N and C-C bonds.
Single-pot access to bisorganoborinates: Applications in zweifel olefination
Music, Arif,Baumann, Andreas N.,Spie?, Philipp,Hilgert, Nicolas,K?llen, Martin,Didier, Dorian
supporting information, p. 2189 - 2193 (2019/04/10)
Zweifel olefination is a catalyst-free reaction that serves alkene functionalization. While most methods employ commercially available boron pinacol esters, we have assembled a sequence in which the two partners of the formal coupling reaction are installed successively, starting from inexpensive boron alkoxides. The in situ formation of bisorganoborinates was accomplished by consecutive reaction of two different organometallic species. This single-pot procedure represents a great advancement in the generation of organoborinates and their involvement in C-C bond formation.
Direct catalytic cross-coupling of alkenyllithium compounds
Hornillos, Valentn,Giannerini, Massimo,Vila, Carlos,Faans-Mastral, Martn,Feringa, Ben L.
, p. 1394 - 1398 (2015/02/19)
A catalytic method for the direct cross-coupling of alkenyllithium reagents with aryl and alkenyl halides is described. The use of a catalyst comprising Pd2(dba)3/XPhos allows for the stereoselective preparation of a wide variety of substituted alkenes in high yields under mild conditions. In addition (1-ethoxyvinyl)lithium can be efficiently converted into substituted vinyl ethers which, after hydrolysis, give readily access to the corresponding methyl ketones in a one pot procedure.
Suzuki cross-coupling reactions between alkenylboronic acids and aryl bromides catalysed by a tetraphosphane-palladium catalyst
Peyroux, Eugenie,Berthiol, Florian,Doucet, Henri,Santelli, Maurice
, p. 1075 - 1082 (2007/10/03)
A range of alkenylboronic acids undergo Suzuki cross-coupling with aryl bromides in good yields in the presence of [PdCl(C3H 5)]2/cis,cis,cis-1,2,3,4-tetrakis[(diphenylphosphanyl) methyl]cyclopentane as a catalyst. A wide variety of 1-arylprop-1-enes, 2-arylprop-1-enes, 2-arylbut-1-enes and 1,1-diarylethylene or styrene derivatives have been prepared. Moreover, the reaction tolerates several functions, such as acetyl, formyl, nitrile or nitro. Furthermore, this catalyst can be used at low loading, even for reactions of sterically hindered substrates. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Electronic effects in asymmetric hydroboration
Garner, Charles M.,Chiang, Shirley,Nething, Matthew,Monestel, Robert
, p. 8339 - 8342 (2007/10/03)
To determine whether electronic effects are operative in asymmetric hydroboration, a series of para-substituted 2-aryl-1-propenes were prepared and reacted with four asymmetric borane reagents. A significant correlation between the electronic nature of the para-substituent and the degree of asymmetric induction was observed only for a chloroborane-ether complex, not for any of several simple alkylboranes. A quantitative analysis of the relative reactivities is also given.
New Near Infrared Absorbing Metal Complex Dyes: Synthesis and Metallochromic Properties of Two Isomeric Ligands, 2-(Dimethylamino)naphtho( and )quinoline-7,12-diones
Yoshida, Katsuhira,Koujiri, Tetsunao,Sakamoto, Eriko,Kubo, Yuji
, p. 1748 - 1752 (2007/10/02)
The Diels-Alder reaction of 5,8-quinolinedione with p-(dimethylamino)styrenes gave new two kinds of isomeric dyes, 2-(dimethylamino)naphthoquinoline-7,12-diones and 2-(dimethylamino)naphthoquinoline-7,12-diones, which showed quite different metallochromic behaviors.Upon addition of metal salts, one of the two isomers showed drastic spectral changes to have an intense absorption band in near infrared region.The color-structure relations were investigated.
