78018-47-0Relevant academic research and scientific papers
Electrochemical-Induced Hydrogenation of Electron-Deficient Internal Olefins and Alkynes with CH3OH as Hydrogen Donor
Qin, Hongyun,Yang, Jianjing,Yan, Kelu,Xue, Yaxuan,Zhang, Meichen,Sun, Xuejun,Wen, Jiangwei,Wang, Hua
supporting information, p. 2104 - 2109 (2021/03/15)
Efficient hydrogenation of electron-deficient internal olefins and alkynes access to saturate ketone with CH3OH as a single hydrogen donor under electrochemical conditions has been successfully developed. This hydrogenation strategy can be used to convert electron-deficient internal olefins and alkynes to saturate ketone under electrochemical conditions with exogenous-reductant and a metal catalyst. Mechanistic studies reveal that radical hydrogenation was involved in this transformation. Notably, various electron-deficient internal olefins and alkynes could be tolerated in such an electrochemical hydrogenation synthetic strategy and can be easily scaled up with good efficiency. (Figure presented.).
Preparation method of beta carbonyl-1, 3-dithiane compound
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Paragraph 0026; 0029; 0030; 0034; 0035; 0050, (2016/10/10)
The invention provides a preparation method of a beta carbonyl-1, 3-dithiane compound. The method consists of the steps of: under the action of protonic acid and/or lewis acid and oxygen, carrying out stirring reaction on 2-chloro-1, 3-dithiane and an alk
Di-tert-Butyl Peroxide-Mediated Atom-Transfer Radical Addition of 2-Chlorodithiane to Aryl Alkynes under Mild Conditions
Lai, Junshan,Tian, Lixia,Liang, Yongping,Zhang, Yuan,Xie, Xingang,Fang, Bowen,Tang, Shouchu
, p. 14328 - 14331 (2015/10/05)
Atom transfer radical addition (ATRA) of 2-chlorodithiane onto aryl alkynes through the use of di-tert-butyl peroxide as an oxidant at room temperature directly affords a variety of synthetically valuable β-chloro-(Z)-vinyl dithianes in good yields with high regioselectivities and without the assistance of any transition metals. It provides an operationally simple pathway to access vinyl dithianes with controlled formation of a new C(sp2) - C bond and a C(sp2) - Cl bond.
Metal-free difunctionalization of alkynes with 2-chlorodithiane for synthesis of β-ketodithianes
Lai, Junshan,Tian, Lixia,Huo, Xing,Zhang, Yuan,Xie, Xingang,Tang, Shouchu
, p. 5894 - 5899 (2015/06/16)
Dithianes are versatile umpolung intermediates in organic synthesis but have rarely been employed in radical cross-coupling reactions. Here we describe the oxidative coupling method for alkyne difunctionalization under metal-catalyst-free conditions. The efficient protocol directly affords a variety of β-ketodithianes in good to excellent yields with high regioselectivities. It provides a general pathway for accessing valuable dithianes with controlled formation of a new C-C bond and a C-O bond via a radical coupling pathway.
Ionic liquid as catalyst and solvent: the remarkable effect of a basic ionic liquid, [bmIm]OH on Michael addition and alkylation of active methylene compounds
Ranu, Brindaban C.,Banerjee, Subhash,Jana, Ranjan
, p. 776 - 782 (2007/10/03)
A basic ionic liquid, 1-methyl-3-butylimidazolium hydroxide, [bmIm]OH, catalyzes the Michael addition of active methylene compounds to conjugated ketones, carboxylic esters and nitriles. It further catalyzes the addition of thiols to α,β-acetylenic ketones and alkylation of 1,3-dicarbonyl and -dicyano compounds. The Michael addition to α,β-unsaturated ketones proceeds in the usual way, giving the monoaddition products, whereas addition to α,β-unsaturated esters and nitriles leads exclusively to the bis-addition products. The α,β-acetylenic ketones undergo double conjugate addition with thiols producing β-keto 1,3-dithio-derivatives. In the alkylation reaction the acyclic 1,3-diketones are monoalkylated, whereas cyclic ketones undergo dialkylation under identical conditions. All these reactions were carried out without any organic solvent. The ionic liquid can also be recycled.
A simple, efficient, and green procedure for the 1,4-addition of thiols to conjugated alkenes and alkynes catalyzed by sodium acetate in aqueous medium
Ranu, Brindaban C.,Mandal, Tanmay
, p. 223 - 227 (2008/02/10)
A benign and inexpensive salt, sodium acetate, efficiently catalyzes 1,4-addition of thiols to a variety of conjugated alkenes such as ?,?-unsaturated ketones, aldehydes, carboxylic esters, nitriles, nitro compounds, and chalcones in aqueous THF. The reac
Scandium triflate as a recyclable catalyst for chemoselective thioacetalization
Kamal, Ahmed,Chouhan, Gagan
, p. 1347 - 1350 (2007/10/03)
Scandium triflate [Sc(OTf)3] has been found to be an extremely efficient and recyclable catalyst for the addition of ethanethiol, 1,2-ethanedithiol and 1,3-propanedithiol to both aromatic and aliphatic aldehydes. In addition, by employing this catalyst, high chemoselective thioacetalization of carbonyl compounds has been achieved.
Chemoselective conjugate 1,4-reduction of α-oxoketene dithioacetals with zinc in acetic acid: Synthesis of β-oxodithioacetals
Rao, Ch. Srinivasa,Patro, Balaram,Ila, Hiriyakkanavar,Junjappa, Hiriyakkanavar
, p. 57 - 59 (2007/10/03)
Acyl ketene dithioacetals 1 and 3 undergo highly chemoselective conjugate 1,4-reduction with zinc in acetic acid to give β-oxodithioacetals 2 and 4 in high yields.
Oxidative Generation of Thioalkyl Cations from 2-Tributylstannyl-1,3-dithianes and 1-(Tributylstannyl)alkyl Sulfides and Their Reactions with Olefinic Nucleophiles
Narasaka, Koichi,Arai, Noriyoshi,Okauchi, Tatsuo
, p. 2995 - 3003 (2007/10/02)
2-Tributylstannyl-1,3-dithianes and 1-(tributylstannyl)alkyl sulfides are oxidized with ammonium hexanitratocerate(IV) or ferrocenium hexafluorophosphate to generate their cation radicals, which dissociate into the carbocations and tributylstannyl radical
