1030-23-5Relevant articles and documents
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
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
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
Metal-free one-pot α-benzoxylation of benzylic alcohols with acids or aldehydes
Zhu, Yefu,Zheng, Yong,Song, Weibin,Wei, Bole,Xuan, Lijiang
, 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.