3480-96-4Relevant academic research and scientific papers
Highly efficient Ru(ii)-alkylidene based Hoveyda-Grubbs catalysts for ring-closing metathesis reactions
Al-Awadi, Nouria A.,Al-Enezi, Mariam Y.,Ibrahim, Yehia A.,John, Elizabeth
, p. 37866 - 37876 (2021/12/09)
Three novel phosphine-free Ru-alkylidenes (7a-7c) have been synthesized and utilized as efficient catalysts for ring closing metathesis (RCM) reaction. Spectroscopic data, i.e. NMR and HRMS, along with single crystal X-ray diffraction analysis, were used
Synthesis of homoallylic amines and acylhydrazides by tin powder-promoted multicomponent one-pot allylation reactions
Ma, Junyan,Huang, Danfeng,Wang, Ke-Hu,Xu, Yanli,Chong, Siying,Su, Yingpeng,Fu, Ying,Hu, Yulai
, p. 571 - 576 (2016/07/16)
An efficient process for the synthesis of homoallylic amines and N′-homoallylic hydrazides is developed from the one-pot reaction of carbonyl compounds, amines or N-acylhydrazines, allyllic bromide and tin powder using water as solvent. N-Acylhydrazines are found to be more reactive than amines in these processes. They can react not only with aldehydes but also with ketones to give the corresponding N′-homoallylic hydrazides. Copyright
Facet-Dependent Catalytic Activity of Palladium Nanocrystals in Tsuji-Trost Allylic Amination Reactions with Product Selectivity
Chanda, Kaushik,Rej, Sourav,Liu, Shu-Ya,Huang, Michael H.
, p. 1813 - 1817 (2015/06/23)
Pd nanocubes, cuboctahedra, and octahedra with good size control were used to catalyze C-N bond formation in the Tsuji-Trost allylic amination reaction of aniline. Nanocubes gave either monoallylaniline or diallylaniline depending on the amount of allyl bromide used, but the octahedra and cuboctahedra only gave mixtures of monoallylaniline and diallylaniline under the same reaction conditions. The Pd nanocubes were stable over multiple cycles of the reaction. The cubes and octahedra were demonstrated to catalyze the amination reaction by using a wide variety of substituted anilines, but the cubes were the best catalyst with consistently the highest efficiency, product yield, and product selectivity. This work demonstrates that the use of metal nanocrystals with proper facet control is important for catalyzing coupling reactions with product selectivity. Getting into shapes: Pd nanocubes, cuboctahedra, and octahedra with good size control are used to catalyze C-N bond formation in the Tsuji-Trost allylic amination reaction of aniline. The Pd nanocube catalyst gives good product selectivity, whereas the Pd octahedra and cuboctahedra catalysts yield mixtures of products under the same reaction conditions. Furthermore, Pd nanocubes are stable over multiple reaction cycles.
Sequential Oxidative α-Cyanation/Anti-Markovnikov Hydroalkoxylation of Allylamines
Wagner, Alexander,Hampel, Nathalie,Zipse, Hendrik,Ofial, Armin R.
supporting information, p. 4770 - 4773 (2015/10/12)
Iron-catalyzed oxidative α-cyanations at tertiary allylamines in the allylic position are followed by anti-Markovnikov additions of alcohols across the vinylic CC double bonds of the initially generated α-amino nitriles. These consecutive reactions generate 2-amino-4-alkoxybutanenitriles from three reactants (allylamines, trimethylsilyl cyanide, and alcohols) in one reaction vessel at ambient temperature.
Highly selective N-allylation of anilines under microwave irradiation
Liu, Meiyu,Wang, Xie,Sun, Xiaoliang,He, Wei
, p. 2711 - 2714 (2014/05/06)
An easy and rapid procedure for the preparation of a variety of mono- and bis-allylated anilines via the reaction of allyl bromide with a wide range of anilines under microwave irradiation is described. This approach allows use of mild conditions and short reaction times to give high selectivities and excellent yields.
Iron(III)-catalyzed C-H functionalization: Ortho-benzoyloxylation of N,N-dialkylanilines and its application to 1,4-benzoxazepines
Chiranjeevi, Barreddi,Vinayak, Botla,Parsharamulu, Thupakula,PhaniBabu, Vemulapalli S.,Jagadeesh, Bharatam,Sridhar, Balasubramanian,Chandrasekharam, Malapaka
, p. 7839 - 7849 (2015/01/16)
A C-O bond-formation reaction that proceeds through C-H functionalization of N,N-dialkylanilines at the ortho-position is presented. The iron-catalyzed selective ortho-benzoyloxylation follows a polar Friedel-Crafts-like mechanism and is sensitive to the nucleophilicity of the anilines. The benzoyl-oxylation of a variety of N,N-disubstituted anilines and Nphenyl heterocycles is carried out under extremely mild conditions. Furthermore, the methodology has been successfully employed for the generation of 1,4-benzoxazepines and oaminophenols.
Sequential combination of ruthenium-, base-, and gold-catalysis - A new approach to the synthesis of medicinally important heterocycles
Ramachary, Dhevalapally B.,Narayana, Vidadala V.
supporting information; experimental part, p. 3514 - 3522 (2011/08/06)
A general approach to the high-yielding synthesis of medicinally important heterocycles was achieved through the sequential combination of ring-closing metathesis, base-induced ring opening (BIRO), hydroamination, and a Diels-Alder reaction of functionalized allyl-(2-allylphenyl)amines in the presence of a catalytic amount of Grubbs' second-generation catalyst, base (tBuOK), and [AuCl(PPh3)]/AgOTf. Herein, we also demonstrate the important electronic factors in the BIRO of N-substituted-benzo[b]azepines for the regioselective synthesis of functionalized (Z)-N-substituted-2-(buta-1,3-dienyl) phenylamines in very good yields with high purity; these are very good, useful compounds in medicinal chemistry. We also discovered the selective cascade synthesis of privileged hexahydrophenanthridines from (Z)-N-substituted-2-(buta- 1,3-dienyl)phenylamines by gold catalysis in moderate to good yields with >99 % diastereomeric excess. The possible reaction mechanism for the unusual hydroamination followed by [4+2] cycloaddition of functionalized (Z)-N-substituted-2-(buta-1,3-dienyl)phenylamines through gold catalysis is discussed in this work. A novel process for the synthesis of highly substituted, medicinally important heterocycles was achieved through the sequential combination of ring-closing methathesis, base-induced ring opening, hydroamination, and Diels-Alder reaction of functionalized allyl-(2-allylphenyl) amines in the presence of a catalytic amount of [Ru], base, and [Au] (see scheme). Copyright
An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis
Sawadjoon, Supaporn,Samec, Joseph S. M.
scheme or table, p. 2548 - 2554 (2011/05/04)
The synthesis of N-aryl, N-tosyl, and N-alkyl pyrrolines from allyl alcohols and amines has been developed. The reaction sequence includes a palladium-catalyzed allylation step in which non-manipulated allyl alcohol is used to generate the diallylated amine in good to excellent yield. An excess of allyl alcohol was necessary for efficient diallylation of the amine, where the excess alcohol could be recycled three times. For aryl and tosyl amines, Pd[P(OPh)3]4 was used and for benzyl and alkyl amines a catalytic system comprising Pd(OAc)2, PnBu3, and BEt3 was used. Both the electronic properties and the steric influence of the amine affected the efficiency of the allylation. The isolated diallylated amines were transformed into their corresponding pyrrolines by ring-closing metathesis catalyzed by (H2IMes)(PCy3)Cl 2RuCHPh in good to excellent yield. A one-pot reaction was developed in which aniline was transformed into the corresponding pyrroline without isolating the diallylated intermediate. This one-pot reaction was successfully scaled-up to 1 mL of aniline in which the N-phenyl pyrroline was isolated in 95% yield. The versatility of the reaction in which 3-methyl-1-phenyl pyrroline was prepared in two-steps was demonstrated.
Palladium-catalyzed cyclization/cyclopropanation reaction for the synthesis of fused N-containing heterocycles
Nandi, Sukla,Ray, Jayanta K.
scheme or table, p. 6993 - 6997 (2010/02/27)
Palladium-catalyzed cyclization/cyclopropanation can be used to convert a range of substituted cyclic N-aryl allyl/methallyl amines efficiently and selectively to the corresponding fused tetrahydropyridine/cyclopropane-fused isoquinoline derivatives via β
Sequential aza-Claisen rearrangement and ring-closing metathesis as a route to 1-benzazepine derivatives
Ghosh, Debalina,Thander, Latibuddin,Ghosh, Sanjay K.,Chattopadhyay, Shital K.
experimental part, p. 3011 - 3015 (2009/06/27)
A synthetic strategy based on sequential application of aza-Claisen rearrangement and ring-closing metathesis reaction as key steps has been developed for the synthesis of various 1-benzazepine derivatives of pharmaceutical relevance. Georg Thieme Verlag
