1030-23-5Relevant academic research and scientific papers
C–O bond formation via oxidative-coupling pathway in eutectic mixture of choline chloride/urea as a green solvent
Saberi, Dariush,Manouchehri, Neda,Niknam, Khodabakhsh
, p. 680 - 687 (2019)
C–O bond formation between terminal alkenes/benzyl alcohols as an arylcarboxy surrogate and carbonyl compounds in a biodegradable deep eutectic solvent (DES) based on choline chloride and urea was performed. By employment of TBAI as catalyst and TBHP as oxidant, various derivatives of carbonyl compounds were benzylated in α position in good to high yield at 90 °C. Moreover, α-oxybenzoylation of diethyl malonate with carboxylic acids was performed in the above-mentioned DES by employment of NaI as the catalyst and TBHP as the oxidant at 60 °C.
Methylsulfinyl (Dimsyl) anion as umpolung catalyst for the chemoselective cross-benzoin reaction of α-diketones with aldehydes
Bortolini, Olga,Fantin, Giancarlo,Ferretti, Valeria,Fogagnolo, Marco,Giovannini, Pier Paolo,Massi, Alessandro,Pacifico, Salvatore,Ragno, Daniele
, p. 3244 - 3252 (2013)
The hitherto unreported ability of the methylsulfinyl carbanion (dimsyl anion) to generate acyl anion equivalents is described. The dimsyl anion, in fact, efficiently catalyzes chemoselective intermolecular cross-benzoin condensations of diaryl α-diketones (benzils) with various aromatic and aliphatic aldehydes to give the corresponding aryl-aryl and aryl-alkyl benzoin benzoates in an atom-economic fashion. The dimsyl anion acts as an environmentally friendly alternative to the toxic cyanide anion and it is obtained by in situ deprotonation of dimethyl sulfoxide (DMSO) solvent with a catalytic amount of a strong base, potassium tert-butoxide (t-BuOK) the optimal promoter. The assumption that the methylsulfinyl carbanion is the active catalyst in the title transformation is supported by electrospray ionization mass spectrometry (ESI-MS) experiments. Copyright
Copper(I)-Catalyzed α-Acryloyloxylation of Ketones with α,β-Unsaturated Carboxylic Acids To Form α-Acryloyloxy Ketones
Xu, Jing-Wen,Ji, Peng-Yi,Liu, Yu-Feng,Luo, Wei-Ping,Liu, Qiang,Guo, Can-Cheng
, p. 734 - 740 (2017)
An efficient method for the α-C–H acryloyloxylation of ketones with α,β-unsaturated carboxylic acids was developed, using copper(I) as a catalyst. The most concise approach to form α-acryloyloxy ketones is through direct oxidative coupling at the α-C(sp3)–H position of ketones. This method gives the products in high yields, and has a wide substrate scope in terms of both ketones and unsaturated carboxylic acids. A copper(I)-catalyzed reaction mechanism is proposed based on the results of control experiments.
Unified and Benign Synthesis of Spirooxindoles via Bifunctional and Recyclable Iodide-Salt-Catalyzed Oxidative Coupling in Water
Wang, Dangui,Lu, Xunbo,Sun, Shaohan,Yu, Huaibin,Su, Huimin,Wu, Yuzhou,Zhong, Fangrui
, p. 6028 - 6033 (2019)
Herein we develop a novel micellar catalytic system based on amphiphilic bifunctional iodide salts for oxidative intramolecular α-oxygenation and α-amination of carbonyl substrates in water, thus enabling a unified and benign synthesis of various 2-oxindo
One-pot synthesis of acyloxy carbonyl compounds from ketones using a Pybox-copper(II) catalyst
Jia, Wei-Guo,Zhang, Hui,Li, Dan-Dan,Yan, Li-Qin
, p. 27590 - 27593 (2016)
We have described the first efficient one-pot method for the synthesis of acyloxy carbonyl compounds from ketones catalyzed by a Pybox-Cu(ii) complex under mild conditions. A series of α-acyloxy ketone products were obtained in good to excellent yields.
α-Acetoxyarone synthesis via iodine-catalyzed and tert-butyl hydroperoxide-mediateded self-intermolecular oxidative coupling of aryl ketones
Tan, Liquan,Chen, Cui,Liu, Weibing
, p. 1079 - 1084 (2017)
We present a metal-free method for α-acetoxyarone synthesis by self-intermolecular oxidative coupling of aryl ketones using I2?tert-butyl hydroperoxide (TBHP). Under the optimum conditions, various aryl ketones gave the corresponding products i
Preparation method of alpha-acyloxy ketone compounds
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Paragraph 0046-0048, (2020/07/15)
The invention relates to a preparation method of alpha-acyloxy ketone compounds. The preparation method comprises the following steps: adding a ketone compound, a copper catalyst and an organosiliconreagent into an N,N-dialkylamide organic solvent, and reacting at 80 DEG C for 24 hours to obtain the alpha-acyloxy ketone. The ketone compound is used as a raw material, and by activating a C (spa keto-carbonyl group, an efficient, simple and convenient new method for constructing the C(sp)-O bond is successfully realized, and a series of alpha-acyloxy ketone compounds are obtained, so the reaction yield is good, the substrate application range is wide, the operation is simple and convenient, and the reaction has high atom and step economy.
Metal-free one-pot α-benzoxylation of benzylic alcohols with acids or aldehydes
Zhu, Yefu,Zheng, Yong,Song, Weibin,Wei, Bole,Xuan, Lijiang
supporting information, p. 368 - 371 (2018/01/04)
A metal-free strategy has been developed for α-benzoxylation of benzylic alcohols with acids or aldehydes. The reaction proceeds via sequential oxidation and α-benzoxylation in one pot. Importantly, the reactions are performed in metal-free condition and utilize cheap aqueous TBHP as an oxidant, affording α-benzoxy ketones in moderate to good yields.
Copper-catalyzed α-C-H acyloxylation of carbonyl compounds with terminal alkynes
Li, Jiao,Yang, Zan,Yang, Tao,Yi, Jianmin,Zhou, Congshan
supporting information, p. 1581 - 1584 (2018/02/09)
Herein, a copper/TBHP catalyst system for the α-C-H acyloxylation of carbonyl compounds is developed using terminal alkynes as the acyloxy source. A variety of carbonyl compounds and terminal alkynes are tolerated in this reaction. In addition, its possible mechanism is proposed.
Electrocatalytic Dehydrogenative Esterification of Aliphatic Carboxylic Acids: Access to Bioactive Lactones
Zhang, Sheng,Lian, Fei,Xue, Mengyu,Qin, Tengteng,Li, Lijun,Zhang, Xu,Xu, Kun
supporting information, p. 6622 - 6625 (2017/12/26)
A scalable and efficient electrocatalytic dehydrogenative esterification is reported. With an indirect electrolysis strategy, both intra- and intermolecular-type reactions were amenable to this practical method. With n-Bu4NI as the catalyst, un
