14310-29-3Relevant articles and documents
Wilkinson's catalyst catalyzed selective hydrogenation of olefin in the presence of an aromatic nitro function: A remarkable solvent effect
Jourdant, Angelique,Gonzalez-Zamora, Eduardo,Zhu, Jieping
, p. 3163 - 3164 (2002)
Optimal conditions for chlorotris(triphenylphosphine)rhodium(I) (Wilkinson's catalyst) catalyzed selective saturation of a double bond in the presence of a nitro function are developed. Aryl iodide and benzyl ether are also tolerated under these hydrogenation conditions.
Ruthenium-Catalyzed E-Selective Partial Hydrogenation of Alkynes under Transfer-Hydrogenation Conditions using Paraformaldehyde as Hydrogen Source
Fetzer, Marcus N. A.,Tavakoli, Ghazal,Klein, Axel,Prechtl, Martin H. G.
, p. 1317 - 1325 (2021/02/11)
E-alkenes were synthesized with up to 100 % E/Z selectivity via ruthenium-catalyzed partial hydrogenation of different aliphatic and aromatic alkynes under transfer-hydrogenation conditions. Paraformaldehyde as a safe, cheap and easily available solid hydrogen carrier was used for the first time as hydrogen source in the presence of water for transfer-hydrogenation of alkynes. Optimization reactions showed the best results for the commercially available binuclear [Ru(p-cymene)Cl2]2 complex as pre-catalyst in combination with 2,2-bis(diphenylphosphino)-1,1-binaphthyl (BINAP) as ligand (1 : 1 ratio per Ru monomer to ligand). Mechanistic investigations showed that the origin of E-selectivity in this reaction is the fast Z to E isomerization of the formed alkenes. Mild reaction conditions plus the use of cheap, easily available and safe materials as well as simple setup and inexpensive catalyst turn this protocol into a feasible and promising stereo complementary procedure to the well-known Z-selective Lindlar reduction in late-stage syntheses. This procedure can also be used for the production of deuterated alkenes simply using d2-paraformaldehyde and D2O mixtures.
Celite-Polyaniline supported palladium catalyst for chemoselective hydrogenation reactions
Patel, Heta A.,Rawat, Maitreyee,Patel, Arun L.,Bedekar, Ashutosh V.
, (2019/02/26)
Polyaniline coated on particles of celite is used as support to load palladium catalyst. This heterogenized Celite?PANI?Pd system, is used as an efficient catalyst for chemoselective hydrogenation reactions. The catalyst is characterized by usual spectral, analytical techniques and studied for hydrogenation reactions at ambient conditions. The mild reaction conditions allow the control over the reactions and excellent selectivity is achieved in number of conversions. Hydrogenation of a carbon–carbon double bond was favored over other polar π-bond systems, while labile functional groups such as benzyl ether, benzyl esters, cyano, nitro and halogen remained unaffected. Primary amines were converted to N,N-dimethyl amines with formaldehyde, the double bond of coumarin was selectively hydrogenated without opening of the lactone functionality.
Application of novel coupling reaction to preparing carbon-carbon bond structured compounds
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Paragraph 0074-0078, (2019/06/30)
The invention relates to application of a novel coupling reaction to preparing carbon-carbon bond structured compounds and mainly provides a reaction between alkyl indium compounds and halides. The reaction between the alkyl indium compounds and the halides can produce corresponding carbon-carbon structured products. The novel coupling reaction is high in process yield, broad in functional group tolerance and good in compatibility.
Copper(II)-catalyzed preparation of alkylindium compounds and applications in cross-coupling reactions both in aqueous media
Wang, Peng,Chen, Bing-Zhi,Guo, Yi-Cong,Rao, Weidong,Shen, Zhi-Liang
supporting information, (2019/11/11)
An efficient water-based method for the synthesis of alkylindium compound in the presence of a catalytic amount of cheap and readily available CuSO4·5H2O (10 mol%) was developed. The thus-generated alkylindium compounds effectively underwent palladium-catalyzed cross-coupling reactions with a myriad of aryl halides in aqueous media, leading to the cross-coupled products in modest to high yields. The mildness of the formed alkyl organometallics allowed the tolerance to various important functional groups incorporated in both substrates of alkyl iodides and aryl halides.
Cobalt(II)-catalyzed preparation of alkylindium reagents and applications in cross-coupling with aryl halides
Wang, Peng,Song, Xuan-Di,Chen, Bing-Zhi,Rao, Weidong,Shen, Zhi-Liang
, (2019/10/16)
The direct insertion of indium powder into alkyl iodides was found to be efficiently catalyzed by a catalytic amount of cobalt(II) bromide (10 mol%). Upon subjection of the thus-formed alkylindium compounds to palladium-catalyzed cross-coupling reactions with a wide range of aryl halides, a series of cross-coupled products could be obtained in moderate to good yields with the tolerance to many important functional groups.
Alkene hydroboration with pinacolborane catalysed by lithium diisobutyl-: Tert-butoxyaluminum hydride
Jaladi, Ashok Kumar,Shin, Won Kyu,An, Duk Keun
, p. 26483 - 26486 (2019/09/12)
Here we developed a highly efficient alkene hydroboration protocol, showing that various alkyl boronates can be smoothly obtained in good yields by reacting alkenes with pinacolborane (HBpin) in the presence of 5 mol% lithium diisobutyl-tert-butoxyaluminum hydride. The coordination of aluminate ions with lithium cations allowed for effective hydride transfer during hydroboration, and the obtained boronate ester was further used for C-C coupling, trifluoroboronate salt formation, and oxidation to alcohol.
Preparation of Alkyl Indium Reagents by Iodine-Catalyzed Direct Indium Insertion and Their Applications in Cross-Coupling Reactions
Zhi, Man-Ling,Chen, Bing-Zhi,Deng, Wei,Chu, Xue-Qiang,Loh, Teck-Peng,Shen, Zhi-Liang
, p. 3017 - 3023 (2019/02/26)
An efficient method for the synthesis of alkyl indium reagent by means of an iodine-catalyzed direct indium insertion into alkyl iodide in THF is reported. The thus-generated alkyl indium reagents effectively underwent Pd-catalyzed cross-coupling reactions with various aryl halides, exhibiting good compatibility to a variety of sensitive functional groups. By replacing THF with DMA and using 0.75 equiv of iodine, less reactive alkyl bromide could be used as substrate for indium insertion with equal ease.
Cesium carbonate-catalyzed indium insertion into alkyl iodides and their synthetic utilities in cross-coupling reactions
Feng, Xue-Xin,Wu, Zhen,Wang, Qing-Dong,Chen, Bing-Zhi,Rao, Weidong,Yang, Jin-Ming,Shen, Zhi-Liang
, (2019/07/31)
A catalytic amount of cesium carbonate (10?mol%) was found to be capable of effectively catalyzing the insertion of indium powder into alkyl iodides. The thus-generated alkyl indium reagents could readily undergo palladium-catalyzed cross-coupling reactions with a wide variety of aryl halides, showing compatibility to a range of important functional groups.
Bis(bipyridine) ruthenium(ii) bis(phosphido) metalloligand: Synthesis of heterometallic complexes and application to catalytic (E)-selective alkyne semi-hydrogenation
Takemoto, Shin,Kitamura, Manami,Saruwatari, Shuhei,Isono, Atsutaka,Takada, Yoko,Nishimori, Rie,Tsujiwaki, Mina,Sakaue, Naoki,Matsuzaka, Hiroyuki
supporting information, p. 1161 - 1165 (2019/01/28)
The first phosphido derivative of the bis(bipyridine) ruthenium(ii) fragment, cis-[(bpy)2Ru(PPh2)2] ([RuP2]), has been developed and applied as a P-donor metalloligand to form new Ru-Rh, Ru-Ir and Ru2Cu2 heterometallic complexes. The Ru-Ir hydride complex [([RuP2])IrH(NCMe)3][BF4]2 exhibits significant catalytic activity for (E)-selective semi-hydrogenation of alkynes.
