55092-47-2Relevant academic research and scientific papers
Synthesis of chloroesters by the reaction of ethers with acyl chlorides catalyzed by ZnO
Tang, Yuqi,Feng, Chengliang,Yang, Wanfeng,Ji, Min,Wang, Wei,Chen, Junqing
, p. 1 - 8 (2020/07/13)
An efficient method for the synthesis of chloroesters by the reaction of ethers with acyl chlorides catalyzed by nano-ZnO under solvent-free condition at room temperature was described. The method is compatible with a range of ethers including tricyclic ethers, tetracyclic ethers, pentacyclic ethers and hexacyclic ethers and have afforded the products with moderate to good yields. The ZnO could be reused up to three times and the product yield after three cycles is 87%.
Palladium(II) acetate catalyzed acylative cleavage of cyclic and acyclic ethers under neat conditions
Fotie, Jean,Adolph, Brandy R.,Bhatt, Shreya V.,Grimm, Casey C.
supporting information, p. 4648 - 4651 (2017/11/15)
During the development of a palladium catalyzed C–H activation cross-coupling reaction involving acyl halides, it was noted that palladium(II) acetate catalyzes the acylative cleavage of tetrahydrofuran (used as a solvent) at room temperature to afford the corresponding 4-chlorobutyl ester derivative. After optimization, the reaction was shown to work well with epoxides, oxetane and tetrahydrofuran, but only barely with oxanes at room temperature. Acyclic ethers systematically failed to react under similar conditions, but underwent complete conversion in a microwave reactor at 100 °C.
Heavier chalcogenone complexes of bismuth(iii)trihalides: Potential catalysts for acylative cleavage of cyclic ethers
Srinivas, Katam,Suresh, Paladugu,Babu, Chatla Naga,Sathyanarayana, Arruri,Prabusankar, Ganesan
, p. 15579 - 15590 (2015/03/05)
Heavier chalcogenones (S, Se and Te) of imidazole act as versatile ligands to yield a series of mononuclear and dinuclear bismuth(iii)complexes of heavier chalcogenones in excellent yield. These new bismuth heavier chalcogen derivatives are the first structurally characterized molecules, where the bismuth and heavier chalcogen ratio is 1:1. There is only one previous report of a crystal structure of a bismuth(iii)-imidazol selone compound and none with bismuth(iii)-imidazol tellone. The bismuth center in monomeric bismuth chalcogen trihalides depicts pseudo trigonal bipyramidal geometry, while the dimeric bismuth chalcogen trihalides demonstrate distorted square pyramidal geometry. The solid state structures of bismuth chalcogenone derivatives feature rare Bi...π(aryl) interactions. Thus, the centroid of the C6-ring suggests a half sandwich type of bismuth environment in mononuclear and dinuclear bismuth(iii) chalcogenone complexes. Notably, the Bi...π(aryl) interaction is not often noticed for mononuclear bismuth chalcogen compounds. Some of the bismuth(iii) chalcogenone complexes also exhibit C-H...π(aryl), C-H...S and C-H...Cl types of hydrogen bonding. The bismuth-chalcogen bond distance in mononuclear bismuth(iii)tribromide chalcogenone complexes is slightly longer than in mononuclear bismuth(iii)trichloride chalcogenone complexes. A gradual increase in carbon-chalcogen bond distance was observed from the free imidazole-chalcogenone to mononuclear bismuth(iii)trichloride chalcogenones, dinuclear bismuth(iii)trichloride chalcogenones and mononuclear bismuth(iii)tribromide chalcogenones and dinuclear bismuth(iii)tribromide chalcogenones. The UV-vis absorption properties and thermal decomposition properties of imidazol chalcogenones and their bismuth derivatives were investigated. Furthermore, the O-acylative cleavage of cyclic ethers was demonstrated using mononuclear and dinuclear bismuth(iii)complexes of heavier chalcogenones as catalysts. In contrast to bismuth(iii)trichloride and bismuth(iii)tribromide catalysts, mononuclear and dinuclear bismuth(iii)complexes of heavier chalcogenones are very active towards an acylative cleavage of cyclic ethers through a mild and regioselective strategy. In particular, mononuclear imidazolthione-bismuth(iii)trichloride is very active towards O-acylative cleavage of 2-methyl tetrahydrofuran. This journal is
Copper-catalyzed Csp3-O cross-coupling of unactivated alkyl halides with organic peroxides
Chen, Huan-Huan,Wang, Guang-Zu,Han, Jin,Xu, Meng-Yu,Zhao, Yong-Qiang,Xu, Hua-Jian
, p. 212 - 217 (2014/01/06)
An efficient Cu-catalyzed Csp3-O coupling of peroxides with haloalkanes is described. High yields of products were achieved under mild conditions. Significantly, in addition to primary alkyl halides, secondary alkyl halogenated hydrocarbons could also be applied to this system. The new reaction system could tolerate a wide range of organic peroxides.
Synthesis of δ- And ε-cyanoesters by zinc-catalyzed ring-opening of cyclic ethers with acid chlorides and subsequent cyanation
Enthaler, Stephan,Weidauer, Maik
experimental part, p. 168 - 175 (2012/03/27)
In the present study, the zinc-catalyzed cleavage of cyclic ethers with acid halides as nucleophiles to yield chloroesters with different chain length has been investigated in detail. In the presence of straightforward and commercially available zinc salts as pre-catalysts excellent yields and selectivities were feasible. After studying the reaction conditions and the scope of the method, several efforts were carried out to understand the reaction mechanism. The obtained chloroesters were subsequently converted to δ- and ε-cyano esters, which are useful precursors in natural product synthesis. Graphical Abstract: [Figure not available: see fulltext.]
Rhenium complex-catalyzed acylative cleavage of ethers with acyl chlorides
Umeda, Rui,Nishimura, Takashi,Kaiba, Kenta,Tanaka, Toshimasa,Takahashi, Yuuki,Nishiyama, Yutaka
experimental part, p. 7217 - 7221 (2011/10/08)
It was found that rhenium complex was an efficient catalyst for the acylative cleavage of C-O bond of ethers with acyl chlorides. When acyclic ethers were allowed to react with acyl chlorides in the presence of a catalytic amount of ReBr(CO)5, acylative cleavage of C-O bond of acyclic ethers smoothly proceeded to give the corresponding esters in moderate to good yields. Similarly, cyclic ethers were acylative cleaved by acyl chlorides to give the corresponding chloro substituted esters in good yields by the use of Re 2O7 catalyst.
A mild and efficient synthesis of chloroesters by the cleavage of cyclic and acyclic ethers using Bi(NO3)3·5H2O as a catalyst under solvent-free conditions
Suresh,Suryakiran,Venkateswarlu
, p. 1037 - 1040 (2008/09/16)
A facile, efficient synthesis of chloroesters is described. The reaction of cyclic and acyclic ethers with acid chlorides in the presence of catalytic amounts of Bi(NO3)2·5H2O under solvent-free conditions yielded the corresponding chloroesters. Also, the catalyst can be recovered conveniently and reused efficiently for at least six times.
Bi(III) halides as efficient catalysts for the O-acylative cleavage of tetrahydrofurans: An expeditious entry to tetralins
Coles, Simon J.,Costello, James F.,Draffin, William N.,Hursthouse, Michael B.,Paver, Simon P.
, p. 4447 - 4452 (2007/10/03)
The mild (DCM/20°C), quantitative, regioselective, O-acylative cleavage of tetrahydrofurans using organic acid halides with catalytic Bi(III) halides is reported. X-ray crystallography is used to rationalise the failure of the reaction in the case of certain crowded acid chlorides, and a useful aspect of chemoselectivity is revealed. The synthetic potential of this reaction is illustrated with a highly efficient O-acylative cleavage/intramolecular alkylation approach to tetralins.
Group 5 and group 6 metal halides as very efficient catalysts for acylative cleavage of ethers
Guo, Qiaoxia,Miyaji, Taichi,Hara, Ryuichiro,Shen, Baojian,Takahashi, Tamotsu
, p. 7327 - 7334 (2007/10/03)
Group 5 and 6 metal chlorides such as MoCl5, WCl6, NbCl5 and TaCl5 were found as very efficient catalysts for acylative cleavage of the C-O bond of ethers. Compared with conventional Lewis acid catalysts such as ZnCl2, AlCl3, SnCl4 and TiCl4, group 5 and 6 metal chlorides showed better results in the catalytic C-O bond cleavage of dibutyl ether with benzoyl chloride.
Graphite-catalyzed acylative cleavage of ethers with acyl halides
Suzuki, Yoshitada,Matsushima, Masayuki,Kodomari, Mitsuo
, p. 319 - 320 (2007/10/03)
Graphite is found to catalyze acylative cleavage of ethers such as benzylic, allylic, tert-butylic and cyclic ethers with acyl halides to give the corresponding esters in good to excellent yields. Benzylic ether was cleaved chemoselectively, when a variety of other functional groups was present, to produce the corresponding ester along with benzyl halide.
