2707-62-2Relevant articles and documents
Mild catalytic deoxygenation of amides promoted by thorium metallocene
Eisen, Moris S.,Saha, Sayantani
supporting information, p. 12835 - 12841 (2020/10/05)
The organoactinide-catalyzed (Cp*2ThMe2) hydroborated reduction of a wide range of tertiary, secondary, and primary amides to the corresponding amines/amine-borane adductsviadeoxygenation of the amides is reported herein. The catalytic reactions proceed under mild conditions with low catalyst loading and pinacolborane (HBpin) concentration in a selective fashion. Cp*2ThMe2is capable of efficiently catalysing the gram-scale reaction without a drop in efficiency. The amine-borane adducts are successfully converted into free amine products in high conversions, which increases the usefulness of this catalytic system. A plausible mechanism is proposed based on detailed kinetics, stoichiometric, and deuterium labeling studies.
Continuous-Flow Amide and Ester Reductions Using Neat Borane Dimethylsulfide Complex
?tv?s, Sándor B.,Kappe, C. Oliver
, p. 1800 - 1807 (2020/02/27)
Reductions of amides and esters are of critical importance in synthetic chemistry, and there are numerous protocols for executing these transformations employing traditional batch conditions. Notably, strategies based on flow chemistry, especially for amide reductions, are much less explored. Herein, a simple process was developed in which neat borane dimethylsulfide complex (BH3?DMS) was used to reduce various esters and amides under continuous-flow conditions. Taking advantage of the solvent-free nature of the commercially available borane reagent, high substrate concentrations were realized, allowing outstanding productivity and a significant reduction in E-factors. In addition, with carefully optimized short residence times, the corresponding alcohols and amines were obtained in high selectivity and high yields. The synthetic utility of the inexpensive and easily implemented flow protocol was further corroborated by multigram-scale syntheses of pharmaceutically relevant products. Owing to its beneficial features, including low solvent and reducing agent consumption, high selectivity, simplicity, and inherent scalability, the present process demonstrates fewer environmental concerns than most typical batch reductions using metal hydrides as reducing agents.
Ru-Catalyzed Deoxygenative Transfer Hydrogenation of Amides to Amines with Formic Acid/Triethylamine
Pan, Yixiao,Luo, Zhenli,Xu, Xin,Zhao, Haoqiang,Han, Jiahong,Xu, Lijin,Fan, Qinghua,Xiao, Jianliang
supporting information, p. 3800 - 3806 (2019/07/12)
A ruthenium(II)-catalyzed deoxygenative transfer hydrogenation of amides to amines using HCO2H/NEt3 as the reducing agent is reported for the first time. The catalyst system consisting of [Ru(2-methylallyl)2(COD)], 1,1,1-tris(diphenylphosphinomethyl) ethane (triphos) and Bis(trifluoromethane sulfonimide) (HNTf2) performed well for deoxygenative reduction of various secondary and tertiary amides into the corresponding amines in high yields with excellent selectivities, and exhibits high tolerance toward functional groups including those that are reduction-sensitive. The choice of hydrogen source and acid co-catalyst is critical for catalysis. Mechanistic studies suggest that the reductive amination of the in situ generated alcohol and amine via borrowing hydrogen is the dominant pathway. (Figure presented.).
Boron Lewis Acid Promoted Ruthenium-Catalyzed Hydrogenation of Amides: An Efficient Approach to Secondary Amines
Yuan, Ming-Lei,Xie, Jian-Hua,Zhou, Qi-Lin
, p. 3036 - 3040 (2016/10/11)
The hydrogenation of amides to amines has been developed by using the catalyst [Ru(H)2(CO)(Triphos)] (Triphos=1,1,1-tri(diphenylphosphinomethyl)ethane) and catalytic boron Lewis acids such as B(C6F5)3 or BF3?Et2O as additives. The reaction provides an efficient method for the preparation of secondary amines from amides in good yields with high selectivity.
Deoxygenative Hydrogenation of Amides Catalyzed by a Well-Defined Iridium Pincer Complex
Yuan, Ming-Lei,Xie, Jian-Hua,Zhu, Shou-Fei,Zhou, Qi-Lin
, p. 3665 - 3669 (2016/07/06)
The iridium-catalyzed highly chemoselective hydrogenation of amides to amines has been developed. Using a well-defined iridium catalyst bearing a P(O)C(O)P pincer ligand combined with B(C6F5)3, the C-O cleavage products are formed under mild reaction conditions. The reaction provides a new method for the preparation of amines from amides in good yield with high selectivity.
Novel diamides of 2,2′-dipyridyl-6,6′-dicarboxylic acid: Synthesis, coordination properties, and possibilities of use in electrochemical sensors and liquid extraction
Kirsanov,Borisova,Reshetova,Ivanov,Korotkov,Eliseev,Alyapyshev, M. Yu.,Spiridonov,Legin,Vlasov, Yu. G.,Babain
, p. 881 - 890 (2013/04/10)
The procedure was proposed for the synthesis of various dipyridyldiamides. Their various properties in the series of rare-earth elements were studied. The possibility to use the synthe-sized compounds in polymer membranes of electrochemical sensors for th
Assembly of substituted 2-alkylquinolines by a sequential palladium-catalyzed Ci-N and Ci-C bond formation
Matsubara, Yoshio,Hirakawa, Saori,Yamaguchi, Yoshihiro,Yoshida, Zen-Ichi
experimental part, p. 7670 - 7673 (2011/10/05)
Diversity: A range of substituted 2-alkylquinolines can be prepared in a general and efficient synthetic approach that employs mild reaction conditions (see scheme). The synthesis is based on a sequential palladium-catalyzed Ci-N and Ci-C bond formation, followed by palladium-catalyzed aromatization, and results in the formation of the desired compounds in one step. Copyright
Synthesis of novel thrombin inhibitors. Use of ring-closing metathesis reactions for synthesis of P2 cyclopentene- and cyclohexenedicarboxylic acid derivatives
Thorstensson, Fredrik,Kvarnstr?m, Ingemar,Musil, Djordje,Nilsson, Ingemar,Samuelsson, Bertil
, p. 1165 - 1179 (2007/10/03)
The thrombin inhibitory tripeptide D-Phe-Pro-Arg has been mimicked using either cyclopentenedicarboxylic derivatives or a cyclohexenedicarboxylic derivative as surrogate for the P2 proline. In the P3 position, tertiary amides were optimized as D-Phe P3 re
