10346-08-4Relevant academic research and scientific papers
Synthesis of an ionic paramagnetic ruthenium(III) complex and its application as an efficient and recyclable catalyst for the transfer hydrogenation of ketones
Zhou, Chengliang,Zhang, Jing,Dakovic, Marijana,Popovic, Zora,Zhao, Xiaoli,Liu, Ye
, p. 3435 - 3440 (2012)
A novel ionic complex, bis[1-butyl-2-(diphenylphosphanyl)-3- methylimidazolium]tetrachloridoruthenium(III) hexafluorophosphate (2), has been synthesized and fully characterized. The single-crystal X-ray diffraction analysis showed that 2 is composed of an Ru complex cation and PF 6- anion. The cation has a highly symmetrical Ru-centered octahedron geometry with four Cl atoms in the equatorial plane and two imidazolium-substituted phosphane ligands in the axial positions. It exhibits paramagnetism due to the presence of one unpaired electron in the phosphane-ligated low-spin RuIII complex. Complex 2 exhibited good catalytic performance in the transfer hydrogenation of a wide range of ketones by using alcohols as hydrogen donors. Owing to its high polarity, good thermal stability, and insensitivity to moisture and oxygen, complex 2 could be used in six catalytic cycles in the transfer hydrogenation of acetophenone without any obvious loss of activity. A novel ionic complex 2 containing an RuIII cation and PF6- anion has been synthesized. The Ru III cation possesses ideal octahedral geometry and exhibits paramagnetism due to the presence of one unpaired electron in the phosphane-ligated low-spin RuIII complex. Complex 2 proves to be an efficient and recyclable catalyst for the transfer hydrogenation of ketones with alcohols as hydrogen donors. Copyright
Dienediolates of unsaturated carboxylic acids in synthesis. Tandem Michael-Dieckmann synthesis of substituted 2-cyclohexenones
Aurell,Gavina,Gil,Parra,Tortajada,Mestres
, p. 1825 - 1831 (1991)
3,5-Disubstituted 2-Cyclohexenones are prepared by tandem Michael-Diekcmann addition of lithium dienediolates of dimethylacrylic and β-methylcinnamic acids to lithium carboxylates of unsaturated carboxylic acids.
Metal-Free I2-Catalyzed Highly Selective Dehydrogenative Coupling of Alcohols and Cyclohexenones
Liang, Yu-Feng,Yuan, Yizhi,Shen, Tao,Song, Song,Jiao, Ning
supporting information, p. 233 - 240 (2018/02/19)
The I2 catalyzed highly selective oxidative condensation of cyclohexenones and alcohols for the synthesis of aryl alkyl ethers has been described. DMSO is employed as the mild terminal oxidant. This novel methodology offers a metal-free reaction condition, operational simplicity and broad substrate scope to afford valuable products from inexpensive reagents. Various meta-substituted aromatic ethers which are hardly synthesized from the reported methods requiring meta-substituted phenols, are efficiently prepared by the present protocol.
Conversion of Simple Cyclohexanones into Catechols
Liang, Yu-Feng,Li, Xinyao,Wang, Xiaoyang,Zou, Miancheng,Tang, Conghui,Liang, Yujie,Song, Song,Jiao, Ning
supporting information, p. 12271 - 12277 (2016/09/28)
A novel I2-catalyzed direct conversion of cyclohexanones to substituted catechols under mild and simple conditions has been described. This novel transformation is remarkable with the multiple oxygenation and dehydrogenative aromatization processes enabled just by using DMSO as the solvent, oxidant, and oxygen source. This metal-free and simple system demonstrates a versatile protocol for the synthesis of highly valuable substituted catechols and therefore streamlines the synthesis and modification of biologically important molecules for drug discovery.
A highly efficient metal-free approach to: Meta - And multiple-substituted phenols via a simple oxidation of cyclohexenones
Liang, Yu-Feng,Song, Song,Ai, Lingsheng,Li, Xinwei,Jiao, Ning
supporting information, p. 6462 - 6467 (2018/06/08)
A novel and efficient metal-free approach to substituted phenols has been disclosed from simple and readily available cyclohexenones and cyclohexenone equivalents. Dimethyl sulfoxide (DMSO), a simple and common organic reagent, was employed as a mild oxidant in this I2-catalysis, which significantly tolerates various substituents including some easily oxidizable or reducible functionalities. The challenging meta- and multiple-substituted phenols could be well prepared by this method. The metal-free and mild oxidation make this protocol very simple, practical, and easy to handle.
Organocatalytic kinetic resolution via intramolecular aldol reactions: Enantioselective synthesis of both enantiomers of chiral cyclohexenones
Chen, Liujuan,Luo, Sanzhong,Li, Jiuyuan,Li, Xin,Cheng, Jin-Pei
scheme or table, p. 2627 - 2632 (2010/07/05)
Kinetic resolution of 6-aryl-2,6-hexanediones was achieved with chiral secondary amine catalyzed intramolecular aldolization. The current kinetic resolution protocol enables the synthesis of both enantiomers of cyclohexenones with moderate to good enantioselectivity. The Royal Society of Chemistry 2010.
An efficient iron-catalyzed carbon-carbon single-bond cleavage via retro-claisen condensation: A mild and convenient approach to synthesize a variety of esters or ketones
Biswas, Srijit,Maiti, Sukhendu,Jana, Umasish
supporting information; experimental part, p. 2861 - 2866 (2010/08/05)
An efficient iron-salt-catalyzed carbon-carbon bond cleavage occurring through a retro-Claisen condensation reaction has been developed. The reaction is useful for the synthesis of a variety of esters or ketones under mild conditions. This method works under solvent-free conditions without the need of an inert atmosphere. This protocol is also applicable for the one-pot syntheses of ketones through tandem carbon-carbon bond formation (substitution or Michael) followed by a retro-Claisen reaction. However, for Michael adducts, ring annulation takes place subsequently. Notably, this method is very simple, convenient, high yielding, and only a catalytic (5 to 1.0 mol-%) amount of Fe(OTf)3 is needed.
A novel synthetic route for the synthesis of 4,6-diaryl-2-methyl-1,3- benzoxazoles
Sridharan,Muthusubramanian,Sivasubramanian
, p. 1321 - 1330 (2007/10/03)
A new synthetic route was developed for the synthesis of 4,6-diaryl-2-methyl-1,3-benzoxazoles and their hydrogenated derivatives. The target compounds were obtained via the Neber rearrangement from 3,5-diaryl-2-cyclohexen-1-ones. The formation of the isom
Cyclohexenone carboxylates. A versatile source for fused isoxazoles and pyrazoles
Padmavathi,Sharmila,Balaiah,Somasekhar Reddy,Bhaskar Reddy
, p. 2119 - 2126 (2007/10/03)
The 6-carbethoxy-3,5-diarylcyclohex-2-enone (1) was subjected to condensation and 1,3-dipolar cycloaddition reactions to get fused isoxazole and pyrazole derivatives.
Preparation and utility of novel water-tolerant higher-order lanthanoid alkoxide complexes as a base catalyst
Kamaura, Masahiro,Daikai, Kazuhiro,Hanamoto, Takeshi,Inanaga, Junji
, p. 697 - 698 (2007/10/03)
A series of higher-order lanthanoid-lithium mixed-alkoxide complexes have been prepared as a novel water-tolerant base catalyst which effectively promotes the Robinson-type reaction in the presence of water.
