98815-54-4Relevant articles and documents
CROSSLINKABLE DEUTERATED CHARGE TRANSPORTING COMPOUND, AN ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE COMPOUND, AND A SOLUTION FORMULATION
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Paragraph 0096; 0097; 0098, (2019/05/04)
A crosslinkable deuterated charge transporting compound comprising a charge transporting unit and a partially or fully deuterated polymerizable group is disclosed. By introducing partially or fully deuterated polymerizable group, the performance of the re
Cobaloxime-catalyzed hydration of terminal alkynes without acidic promoters
Hou, Shengtai,Yang, Hongjian,Cheng, Bin,Zhai, Hongbin,Li, Yun
, p. 6926 - 6929 (2017/07/10)
Cobaloxime (Co(dmgBF2)2·2H2O), an inexpensive first-row transition-metal complex, catalyzed hydration of terminal alkynes gave the corresponding methyl ketones in good to excellent yields under neutral conditions (additional protic acids and silver salts are not required). A wide range of functional groups, such as allyl ether, benzyl ethers, carboxylic esters, imides, amides, nitro, and halogens, were tolerated. The mild reaction conditions together with the inexpensive feature and easy availability of the catalyst well address the current challenges in the field of alkyne hydration.
Organocatalytic Imidazolium Ionic Liquids H/D Exchange Catalysts
Zanatta, Marcileia,Dos Santos, Francisco P.,Biehl, Cristina,Marin, Graciane,Ebeling, Gunter,Netz, Paulo A.,Dupont, Jairton
supporting information, p. 2622 - 2629 (2017/03/14)
Simple 1,2,3-trialkylimidazolium cation associated with basic anions, such as hydrogen carbonate, prolinate, and imidazolate, is an active catalyst for the H/D exchange reaction of various substrates using CDCl3 as D source, without the addition of any extra bases or metal. High deuterium incorporation (up to 49%) in acidic C-H bonds of ketone and alkyne substrates (pKa from 18.7 to 28.8) was found at room temperature. The reaction proceeds through the fast and reversible deuteration of the 2-methyl H of the imidazolium cation followed by D transfer to the substrate. The IL acts as a neutral base catalyst in which the contact ion pair is maintained in the course of the reaction. The basic active site is due to the presence of a remote basic site in the anion namely, OH of bicarbonate, NH of prolinate, and activated water in the imidazolate anion. Detailed kinetic experiments demonstrate that the reaction is first order on the substrate and pseudozero order relative to the ionic liquid, due to the fast reversible reaction involving the deuteration of the ionic liquid by the solvent.
A simple method for α-position deuterated carbonyl compounds with pyrrolidine as catalyst
Zhan, Miao,Zhang, Tao,Huang, Haoxi,Xie, Yongmei,Chen, Yuanwei
, p. 533 - 539 (2014/08/05)
A simple, cost-effective method for deuteration of carbonyl compounds employing pyrrolidine as catalyst and D2O as deuterium source was described. High degree of deuterium incorporation (up to 99%) and extensive functional group tolerance were achieved. It is the first time that secondary amines are used as catalysts for H/D exchange of carbonyl compounds, which also allow the deuteration of complex pharmaceutically interesting substrates. A possible catalytic mechanism, based on the hydrolysis of 1-pyrrolidino-1- cyclohexene, for this pyrrolidine-catalyzed H/D exchange reaction has been proposed. Pyrrolidine has been shown to be an efficient catalyst for deuteration of carbonyl compounds. The method also allowed the deuteration of complex pharmaceutically interesting substrates. Preliminary experiment showed that the enamine and/or iminium activation modes may be involved. Copyright
DEBROMINATION OF PHENACYL AND BENZYLIC BROMIDES WITH TERTIARY STIBINE AND THE MECHANISTIC CONSIDERATION
Akiba, Kin-ya,Shimizu, Akiyoshi,Ohnari, Hideyuki,Ohkata, Katsuo
, p. 3211 - 3214 (2007/10/02)
Tributylstibine is an efficient reagent for debromination of phenacyl and arylmethyl bromides.The mechanistic difference between stibine and phosphine is discussed briefly.
Reactions of 4-Substituted-2'-Halogenoacetophenones with Grignard Reagents
Crombie, Leslie,Hardy, Robert,Knight, David W.
, p. 1373 - 1380 (2007/10/02)
The initial reaction of 4-substituted 2'-halogenoacetophenones with an excess of methyl Grignard reagent is shown to be an attack at the 1'-carbonyl to form a halohydrin salt.The various reactions which then follow are substituent dependent.In the 4-hydroxy case the only product is 1-(4-hydroxyphenyl)-2-methylpropan-2-ol (13) which arises via a -aryl shift with simultaneous elimination of magnesium halide.When the substituent is 4-methoxy, a second pathway becomes important involving epoxide formation and a subsequent -hydride migration to the benzylic position, or attack of the Grignard reagent at the benzylic carbon of the epoxide.When the substituent is 4-bromo, the reaction proceeds exclusively via the epoxide and, following a -hydride shift, leads to the isomeric butanols (33) and (34).The reasons underlying such diversity of reactivity are discussed.
