6050-58-4Relevant academic research and scientific papers
Iron-Catalyzed Anti-Markovnikov Hydroamination and Hydroamidation of Allylic Alcohols
Ma, Wei,Zhang, Xiaohui,Fan, Juan,Liu, Yuxuan,Tang, Weijun,Xue, Dong,Li, Chaoqun,Xiao, Jianliang,Wang, Chao
supporting information, p. 13506 - 13515 (2019/09/09)
Hydroamination allows for the direct access to synthetically important amines. Controlling the selectivity of the reaction with efficient, widely applicable, and economic catalysts remains challenging, however. This paper reports an iron-catalyzed formal anti-Markovnikov hydroamination and hydroamidation of allylic alcohols, which yields γ-amino and γ-amido alcohols, respectively. Homoallylic alcohol is also feasible. The catalytic system, consisting of a pincer Fe-PNP complex (1-4 mol %), a weak base, and a nonpolar solvent, features exclusive anti-Markovnikov selectivity, broad substrate scope (>70 examples), and good functional group tolerance. The reaction could be performed at gram scale and applied to the synthesis of drug molecules and heterocyclic compounds. When chiral substrates are used, the stereochemistry and enantiomeric excess are retained. Further application of the chemistry is seen in the functionalization of amino acids, natural products, and existing drugs. Mechanistic studies suggest that the reaction proceeds via two cooperating catalytic cycles, with the iron complex catalyzing a dehydrogenation/hydrogenation process while the amine substrate acts as an organocatalyst for the Michael addition step.
A Commercially Available and User-Friendly Catalyst for Hydroamination Reactions under Technical Conditions
Zelenay, Benjamin,Munton, Peter,Tian, Xiaojie,Díez-González, Silvia
, p. 4725 - 4730 (2019/08/01)
The activity of a simple, commercially available copper salt, [Cu(NCMe)4](BF4) in intramolecular hydroamination reactions of alkynes and allenes is presented. Reactions were successfully carried out in technical acetonitrile in the presence of air. While attempts of alkene hydroamination failed, this catalyst was also found active in intermolecular aza-Michael reactions.
Palladium nanocatalysts in glycerol: Tuning the reactivity by effect of the stabilizer
Reina, Antonio,Serrano-Maldonado, Alejandro,Teuma, Emmanuelle,Martin, Erika,Gómez, Montserrat
, p. 22 - 27 (2017/10/24)
Palladium nanoparticles (PdNPs) prepared in neat glycerol containing TPPTS (tris(3-sulfophenyl)phosphine trisodium salt) or cinchona-based alkaloids (cinchonidine, quinidine) as capping agents, were applied as catalysts in fluoride-free Hiyama couplings and conjugate additions with the aim of evaluating the influence of the stabilizer in the catalytic reactivity. Therefore, PdNPs stabilized by phosphine favored C–C cross-couplings, whereas those containing alkaloids showed enhanced suitability for C–C homo-couplings and conjugate additions. The metal/stabilizer coordination mode, i.e. Pd–P dative bond and π-π interaction between quinoline moiety and palladium surface, is certainly key for the stabilization of different active metallic species and then promoting distinctive catalytic pathways.
Gaining in pan-affinity towards sigma 1 and sigma 2 receptors. SAR studies on arylalkylamines
Rossi, Daniela,Rui, Marta,Di Giacomo, Marcello,Schepmann, Dirk,Wünsch, Bernhard,Monteleone, Stefania,Liedl, Klaus R.,Collina, Simona
, p. 11 - 19 (2016/12/22)
Sigma Receptor (SR) modulators are involved in different signal transduction pathways, representing important pharmacological/therapeutic tools in several pathological conditions, such as neurodegenerative diseases and cancers. To this purpose, numerous c
A formal anti-Markovnikov hydroamination of allylic alcohols via tandem oxidation/1,4-conjugate addition/1,2-reduction using a Ru catalyst
Nakamura, Yushi,Ohta, Tetsuo,Oe, Yohei
supporting information, p. 7459 - 7462 (2015/05/04)
A formal anti-Markovnikov hydroamination of allylic alcohols using a Ru catalyst via tandem oxidation/1,4-conjugate addition/1,2-reduction was developed. Thus, the reaction of allylic alcohols with amines was performed in the presence of the catalyst generated from RuClH(CO)(PPh3)3 and 2,6-bis(n-butyliminomethyl)pyridine in situ to afford the corresponding γ-amino alcohols efficiently. This journal is
[CH3COO]: Efficient and recyclable catalyst for aza-Michael addition of α, β-unsaturated compounds and amines under solvent-free conditions
Gao, Xiaochong,Gao, Ruichang
, p. 9101 - 9112 (2015/03/04)
The recyclable ionic liquid [ADPQ][CH3COO] has been used as catalyst for aza-Michael addition of amines to α, β-unsaturated compounds to produce β-amino compounds. The reactions were complete in a few hours with high yields. The ionic liquid can be recycled and reused six times without noticeable decrease of catalytic activity.
Heterobimetallic Pd-Sn catalysis: Michael addition reaction with C-, N-, O-, and S-nucleophiles and in situ diagnostics
Das, Debjit,Pratihar, Sanjay,Roy, Sujit
, p. 2430 - 2442 (2013/04/23)
An efficient Michael addition reaction of differently substituted enones with carbon, sulfur, oxygen, and nitrogen nucleophiles has been achieved by a new heterobimetallic "Pd-Sn" catalyst system. The nature of the catalytically relevant species and their
A novel method for biomimetic synthesis of Mannich bases
Guo, Yuan,An, Jing,Lu, Zhenhuan,Peng, Mengjiao
experimental part, p. 1561 - 1564 (2012/10/07)
Since the early studies of Mannich, Mannich reaction has become an important tool for the synthesis of new compounds. Mannich bases can be either directly employed or used as intermediates. In this work, the one-carbon unit transfer reaction of tetrahydrofolate coenzyme was initiated. 1,3-Dimethylimidazolidine as a new tetrahydrofolate coenzyme model at formaldehyde oxidation level was used to react with ketone having active hydrogen atoms and amine to give the corresponding Mannich base in good yield by a covert Mannich reaction. A novel method for biomimetic synthesis of various Mannich bases is provided. 1,3-Dimethylimidazolidine as a new tetrahydrofolate coenzyme model at formaldehyde oxidation level was used to react with ketone having active hydrogen atoms and amine to give the corresponding Mannich base in good yield by a covert Mannich reaction. A novel method for biomimetic synthesis of various Mannich bases is provided. Copyright
Aza-Michael reactions in water using functionalized ionic liquids as the recyclable catalysts
Liu,Lu,Gu,Lu
experimental part, p. 775 - 781 (2012/06/18)
Some recyclable SO3H-functionalized ionic liquids have been used as catalysts in water for the aza-Michael reactions of amines with α,β-unsaturated compounds to produce β-amino compounds. High yields of the products, short reaction times, mild reaction conditions, simple experimental procedure, reusable catalysts and no obvious loss of the catalytic activity make this protocol a contribution to organic chemistry.
