cas 26177-44-6, 4-Bromobenzylamine hydrochloride

Articles about 26177-44-6Total 30 be found

Article title
Article abstract
Author
Journal number and time
Download

Preparation method of intermediate p-bromobenzylamine hydrochloride for synthesizing protein degradation agent 1
The invention discloses a preparation method of an intermediate p-bromobenzylamine hydrochloride for synthesizing a protein degradation agent 1, which comprises the following steps: sequentially adding a certain amount of p-bromobenzyl bromide, sodium diformylamide and an ether inert solvent, conducting reacting for 10-15 hours at a certain temperature, cooling the reaction system to room temperature, and conducting filtering to obtain filtrate; concentrating the filtrate under reduced pressure to remove the solvent to obtain a residue, sequentially adding a certain amount of ethanol and concentrated hydrochloric acid into the residue, conducting reacting for 15-20 hours at a certain temperature, and cooling a formed reaction system to room temperature; and then adding a certain amount of ethyl acetate for crystallization, and conducting filtering and drying to obtain the p-bromobenzylamine hydrochloride. According to the synthesis method of the p-bromobenzylamine hydrochloride, dangerous chemicals sodium azide and hydrazine hydrate used in preparation of the p-bromobenzylamine hydrochloride reported in existing literatures are avoided, meanwhile, the three wastes are few, the yield is high, and the synthesis method has the advantages of being easy to operate, high in safety, good in product quality, low in cost and the like and is convenient for large-scale production.
-
Paragraph 0018; 0020-0024; 0026-0029; 0031-0034; 0036-0038

(2021/06/02)

Silver-Catalyzed Hydroboration of C-X (X = C, O, N) Multiple Bonds
AgSbF6 was developed as an effective catalyst for the hydroboration of various unsaturated functionalities (nitriles, alkenes, and aldehydes). This atom-economic chemoselective protocol works effectively under low catalyst loading, base- A nd solvent-free moderate conditions. Importantly, this process shows excellent functional group tolerance and compatibility with structurally and electronically diverse substrates (>50 examples). Mechanistic investigations revealed that the reaction proceeds via a radical pathway. Further, the obtained N,N-diborylamines were showcased to be useful precursors for amide synthesis.
Pandey, Vipin K.,Tiwari, Chandra Shekhar,Rit, Arnab
supporting information
p. 1681 - 1686
(2021/03/03)

Aluminum Metal-Organic Framework-Ligated Single-Site Nickel(II)-Hydride for Heterogeneous Chemoselective Catalysis
The development of chemoselective and heterogeneous earth-abundant metal catalysts is essential for environmentally friendly chemical synthesis. We report a highly efficient, chemoselective, and reusable single-site nickel(II) hydride catalyst based on robust and porous aluminum metal-organic frameworks (MOFs) (DUT-5) for hydrogenation of nitro and nitrile compounds to the corresponding amines and hydrogenolysis of aryl ethers under mild conditions. The nickel-hydride catalyst was prepared by the metalation of aluminum hydroxide secondary building units (SBUs) of DUT-5 having the formula of Al(μ2-OH)(bpdc) (bpdc = 4,4′-biphenyldicarboxylate) with NiBr2 followed by a reaction with NaEt3BH. DUT-5-NiH has a broad substrate scope with excellent functional group tolerance in the hydrogenation of aromatic and aliphatic nitro and nitrile compounds under 1 bar H2 and could be recycled and reused at least 10 times. By changing the reaction conditions of the hydrogenation of nitriles, symmetric or unsymmetric secondary amines were also afforded selectively. The experimental and computational studies suggested reversible nitrile coordination to nickel followed by 1,2-insertion of coordinated nitrile into the nickel-hydride bond occurring in the turnover-limiting step. In addition, DUT-5-NiH is also an active catalyst for chemoselective hydrogenolysis of carbon-oxygen bonds in aryl ethers to afford hydrocarbons under atmospheric hydrogen in the absence of any base, which is important for the generation of fuels from biomass. This work highlights the potential of MOF-based single-site earth-abundant metal catalysts for practical and eco-friendly production of chemical feedstocks and biofuels.
Antil, Neha,Kumar, Ajay,Akhtar, Naved,Newar, Rajashree,Begum, Wahida,Dwivedi, Ashutosh,Manna, Kuntal
p. 3943 - 3957
(2021/04/12)

Phosphine-Free Manganese Catalyst Enables Selective Transfer Hydrogenation of Nitriles to Primary and Secondary Amines Using Ammonia-Borane
Herein we report the synthesis of primary and secondary amines by nitrile hydrogenation, employing a borrowing hydrogenation strategy. A class of phosphine-free manganese(I) complexes bearing sulfur side arms catalyzed the reaction under mild reaction conditions, where ammonia-borane is used as the source of hydrogen. The synthetic protocol is chemodivergent, as the final product is either primary or secondary amine, which can be controlled by changing the catalyst structure and the polarity of the reaction medium. The significant advantage of this method is that the protocol operates without externally added base or other additives as well as obviates the use of high-pressure dihydrogen gas required for other nitrile hydrogenation reactions. Utilizing this method, a wide variety of primary and symmetric and asymmetric secondary amines were synthesized in high yields. A mechanistic study involving kinetic experiments and high-level DFT computations revealed that both outer-sphere dehydrogenation and inner-sphere hydrogenation were predominantly operative in the catalytic cycle.
Sarkar, Koushik,Das, Kuhali,Kundu, Abhishek,Adhikari, Debashis,Maji, Biplab
p. 2786 - 2794
(2021/03/03)

A cobalt phosphide catalyst for the hydrogenation of nitriles
The study of metal phosphide catalysts for organic synthesis is rare. We present, for the first time, a well-defined nano-cobalt phosphide (nano-Co2P) that can serve as a new class of catalysts for the hydrogenation of nitriles to primary amines. While earth-abundant metal catalysts for nitrile hydrogenation generally suffer from air-instability (pyrophoricity), low activity and the need for harsh reaction conditions, nano-Co2P shows both air-stability and remarkably high activity for the hydrogenation of valeronitrile with an excellent turnover number exceeding 58000, which is over 20- to 500-fold greater than that of those previously reported. Moreover, nano-Co2P efficiently promotes the hydrogenation of a wide range of nitriles, which include di- and tetra-nitriles, to the corresponding primary amines even under just 1 bar of H2 pressure, far milder than the conventional reaction conditions. Detailed spectroscopic studies reveal that the high performance of nano-Co2P is attributed to its air-stable metallic nature and the increase of the d-electron density of Co near the Fermi level by the phosphidation of Co, which thus leads to the accelerated activation of both nitrile and H2. Such a phosphidation provides a promising method for the design of an advanced catalyst with high activity and stability in highly efficient and environmentally benign hydrogenations. This journal is
Jitsukawa, Koichiro,Mitsudome, Takato,Mizugaki, Tomoo,Nakata, Ayako,Sheng, Min,Yamasaki, Jun
p. 6682 - 6689
(2020/08/24)

Silicon hydrogenation reaction method of organic boron and inorganic alkali catalysis amide (by machine translation)
The method is characterized in that organic boron and inorganic bases are used as catalysts, silane is used as a reducing agent, primary amide is reduced to primary amine or dehydration dinitrile, the secondary amide is reduced to a secondary amine or aldimine, and the tertiary amide is reduced to tertiary amine. The method has the advantages of simple operation, mild reaction conditions, wide substrate universality, good functional group compatibility and the like, and has the characteristics of good stability, cheap and accessible catalyst, simple and convenient operation, high practicality and the like. (by machine translation)
-
Paragraph 0134-0140; 0150-0153

(2020/08/18)

An imidazolin-2-iminato ligand organozinc complex as a catalyst for hydroboration of organic nitriles
The reaction of diethylzinc with imidazolin-2-imines (ImRNH, R = Dipp (2,6-diisopropylphenyl)), Mes (2,4,6-trimethylphenyl), and tBu (tert-butyl) afforded the corresponding dimeric zinc(ii) imidazolin-2-iminato complexes [{(ImRN)Zn(CH2CH3)}2] (R = Dipp, 1a; R = Mes, 1b; R = tBu, 1c). The zinc complexes were characterised using spectroscopic techniques and the molecular structure of complex 1b was established by single-crystal X-ray diffraction analysis. Complex 1c was used as a catalyst for the chemo-selective hydroboration of organic nitriles with pinacolborane (HBpin) at ambient temperature to obtain diborylamines of a broad substrate scope in high yield. Zinc complex 1c exhibits a versatile substrate scope and good functional group tolerance for catalytic hydroboration reactions. A most plausible mechanism is proposed on the basis of the kinetic study.
Das, Suman,Bhattacharjee, Jayeeta,Panda, Tarun K.
supporting information
p. 16812 - 16818
(2019/11/14)

A BEt3-Base catalyst for amide reduction with silane
Reported herein is the development of a simple but practical catalytic system for the selective reduction of amides with hydrosilane or hydrosiloxane. Low-cost and readily available triethylborane (1.0 M in THF), in combination with a catalytic amount of an alkali metal base, was found to catalyze the reduction of all three amide classes (tertiary, secondary, and primary amides) to form amines under mild conditions. In addition, the selective transformation of secondary amides to aldimines and primary amides to nitriles can also be achieved by using a proper combination of BEt3 and base. The scope of these BEt3-base-catalyzed amide hydrosilylation reactions has been explored in depth. Preliminary results of mechanistic studies suggest a modified Piers' silane Si-H···B activation mode wherein the hydride abstraction by BEt3 is promoted by the coordination of an alkoxide or hydroxide anion to the Si center.
Yao, Wubing,Fang, Huaquan,He, Qiaoxing,Peng, Dongjie,Liu, Guixia,Huang, Zheng
(2019/05/22)

A BEt3-Base Catalyst for Amide Reduction with Silane
Reported herein is the development of a simple but practical catalytic system for the selective reduction of amides with hydrosilane or hydrosiloxane. Low-cost and readily available triethylborane (1.0 M in THF), in combination with a catalytic amount of an alkali metal base, was found to catalyze the reduction of all three amide classes (tertiary, secondary, and primary amides) to form amines under mild conditions. In addition, the selective transformation of secondary amides to aldimines and primary amides to nitriles can also be achieved by using a proper combination of BEt3 and base. The scope of these BEt3-base-catalyzed amide hydrosilylation reactions has been explored in depth. Preliminary results of mechanistic studies suggest a modified Piers' silane Si-H···B activation mode wherein the hydride abstraction by BEt3 is promoted by the coordination of an alkoxide or hydroxide anion to the Si center.
Yao, Wubing,Fang, Huaquan,He, Qiaoxing,Peng, Dongjie,Liu, Guixia,Huang, Zheng
p. 6084 - 6093
(2019/05/24)

Primary amides to amines or nitriles: A dual role by a single catalyst
We report a manganese-catalyzed hydrosilylative reduction of various primary amides to amines (25 examples). On simple modification of the reaction conditions such as in the presence of a catalytic amount of secondary amide, the same catalyst can transform the primary amides into intermediate nitrile compounds (16 examples) in excellent yields. This is the first example where such a controlled catalytic transformation of primary amides to amines or nitriles with a single catalyst has been demonstrated.
Das, Hari S.,Das, Shyamal,Dey, Kartick,Singh, Bhagat,Haridasan, Rahul,Das, Arpan,Ahmed, Jasimuddin,Mandal, Swadhin K.
supporting information
p. 11868 - 11871
(2019/10/11)

Old Concepts, New Application – Additive-Free Hydrogenation of Nitriles Catalyzed by an Air Stable Alkyl Mn(I) Complex
An efficient additive-free manganese-catalyzed hydrogenation of nitriles to primary amines with molecular hydrogen is described. The pre-catalyst, a well-defined bench-stable alkyl bisphosphine Mn(I) complex fac-[Mn(dpre)(CO)3(CH3)] (dpre=1,2-bis(di-n-propylphosphino)ethane), undergoes CO migratory insertion into the manganese-alkyl bond to form acyl complexes which upon hydrogenolysis yields the active coordinatively unsaturated Mn(I) hydride catalyst [Mn(dpre)(CO)2(H)]. A range of aromatic and aliphatic nitriles were efficiently and selectively converted into primary amines in good to excellent yields. The hydrogenation of nitriles proceeds at 100 °C with a catalyst loading of 2 mol % and a hydrogen pressure of 50 bar. Mechanistic insights are provided by means of DFT calculations. (Figure presented.).
Weber, Stefan,Veiros, Luis F.,Kirchner, Karl
supporting information
p. 5412 - 5420
(2019/11/13)

Catalytic Reduction of Nitriles by Polymethylhydrosiloxane Using a Phenalenyl-Based Iron(III) Complex
The reduction of nitriles to primary amines using an inexpensive silane such as polymethylhydrosiloxane (PMHS) is an industrially important reaction. Herein we report the synthesis of an earth-abundant Fe(III) complex bearing a phenalenyl-based ligand that was characterized by mass spectroscopy, elemental analysis, cyclic voltammetry, and single-crystal X-ray diffraction. The complex showed excellent catalytic activity toward reduction of aromatic, heteroaromatic, aliphatic, and sterically crowded nitriles to produce primary amines using polymethylhydrosiloxane (PMHS).
Das, Shyamal,Das, Hari Sankar,Singh, Bhagat,Haridasan, Rahul Koottanil,Das, Arpan,Mandal, Swadhin K.
supporting information
p. 11274 - 11278
(2019/09/10)

Switching the Selectivity of Cobalt-Catalyzed Hydrogenation of Nitriles
Previous studies of base metals for catalytic hydrogenation of nitriles to primary amines or secondary aldimines focus on designing complexes with elaborate structures. Herein, we report "twin" catalytic systems where the selectivity of nitrile hydrogenation can be tuned by including or omitting the ligand HN(CH2CH2PiPr2)2 (iPrPNHP). Simply treating CoBr2 with NaHBEt3 generates cobalt particles, which can catalyze the hydrogenation of nitriles to primary amines with high selectivity and broad functional group tolerance. Ligating CoBr2 with iPrPNHP followed by the addition of NaHBEt3, however, forms a homogeneous catalyst favoring secondary aldimines for both hydrogenation and hydrogenative coupling of benzonitrile.
Dai, Huiguang,Guan, Hairong
p. 9125 - 9130
(2018/09/21)

Hydrogenation of Nitriles and Ketones Catalyzed by an Air-Stable Bisphosphine Mn(I) Complex
Efficient hydrogenations of nitriles and ketones with molecular hydrogen catalyzed by a well-defined bench-stable bisphosphine Mn(I) complex are described. These reactions are environmentally benign and atomically economic, implementing an inexpensive, earth-abundant nonprecious metal catalyst. A range of aromatic and aliphatic nitriles and ketones were efficiently converted into primary amines and alcohols, respectively, in good to excellent yields. The hydrogenation of nitriles proceeds at 100 °C with catalyst loading of 2 mol % and 20 mol % base (t-BuOK), while the hydrogenation of ketones takes place already at 50 °C, with a catalyst loading of 1 mol % and 5 mol % of base. In both cases, a hydrogen pressure of 50 bar was applied.
Weber, Stefan,St?ger, Berthold,Kirchner, Karl
supporting information
p. 7212 - 7215
(2018/11/25)

Exhaustive Chemoselective Reduction of Nitriles by Catalytic Hydrosilylation Involving Cooperative Si-H Bond Activation
A chemoselective method for the catalytic hydrosilylation of nitriles to either the imine or amine oxidation level is reported. The chemoselectivity is controlled by the hydrosilane used. The usefulness of the nitrile-to-amine reduction is demonstrated for a diverse set of aromatic and aliphatic nitriles, and the amines are easily isolated after hydrolysis as their hydrochloride salts. This exhaustive nitrile reduction proceeds at room temperature.
Wübbolt, Simon,Oestreich, Martin
supporting information
p. 2411 - 2414
(2017/10/03)

Stable and Inert Cobalt Catalysts for Highly Selective and Practical Hydrogenation of C≡N and C=O Bonds
Novel heterogeneous cobalt-based catalysts have been prepared by pyrolysis of cobalt complexes with nitrogen ligands on different inorganic supports. The activity and selectivity of the resulting materials in the hydrogenation of nitriles and carbonyl compounds is strongly influenced by the modification of the support and the nitrogen-containing ligand. The optimal catalyst system ([Co(OAc)2/Phenα-Al2O3]-800 = Cat. E) allows for efficient reduction of both aromatic and aliphatic nitriles including industrially relevant dinitriles to primary amines under mild conditions. The generality and practicability of this system is further demonstrated in the hydrogenation of diverse aliphatic, aromatic, and heterocyclic ketones as well as aldehydes, which are readily reduced to the corresponding alcohols.
Chen, Feng,Topf, Christoph,Radnik, J?rg,Kreyenschulte, Carsten,Lund, Henrik,Schneider, Matthias,Surkus, Annette-Enrica,He, Lin,Junge, Kathrin,Beller, Matthias
supporting information
p. 8781 - 8788
(2016/08/02)

A method for the production of primary amines
The invention relates to the field of chemical industry and particularly relates to a method for preparing primary amine by using the raw materials including halogenated hydrocarbon (or hydrocarbon alcohol sulfonate) and ammonia water (or formamide). The method comprises the following three steps: (1) imidization: 3,4-diarylfuran-2,5-diketone (I) reacts with ammonia (or formamide) and the like to obtain 3,4-diaryl-1H-pyrrole-2,5-diketone (II); (2) N-hydrocarbylation: 3,4-diaryl-1H-pyrrole-2,5-diketone (II) generates an N-hydrocarbylation reaction with halogenated hydrocarbon (or hydrocarbon alcohol sulfonate) in the presence of alkali to obtain N-hydrocarbyl-3,4-diaryl-1H-pyrrole-2,5-diketone (III); and (3) hydrolysis: N-hydrocarbyl-3,4-diaryl-1H-pyrrole-2,5-diketone (III) is subjected to alkali hydrolysis to obtain primary amine and the generated 2,3-diaryl maleate is subjected to acid treatment and automatic ring closing to form 3,4-diaryl furan-2,5-diketone (I) which is subjected to imidization and directly applied to the N-hydrocarbylation reaction. The method provided by the invention has the characteristics that the 3,4-diaryl furan-2,5-diketone can be circularly used at a high recovery rate, the molar ratio of the raw materials is low, and the yield of the product primary amine is high.
-
Paragraph 0192; 0193

(2016/10/09)

Direct cycle between co-product and reactant: An approach to improve the atom economy and its application in the synthesis and protection of primary amines
Two important goals of green chemistry are to maximize the efficiency of reactants and to minimize the production of waste. In this study, a novel approach to improve the atom economy of a chemical process was developed by incorporating a direct cycle between a co-product and a reactant of the same reaction. To demonstrate this concept, recoverable 3,4-diphenylmaleic anhydride (1) was designed and used for the atom-economical synthesis of aliphatic primary amines from aqueous ammonia. In each individual cycle, only ammonia and alkyl halide were consumed, and 1 was recovered in nearly a quantitative yield. In this approach for developing atom-economical protecting agents, 1 showed good performance as a recoverable protecting agent for primary amines. The broad substrate scope, good tolerance to various reaction conditions, and high reaction and recovery rates make 1 a valuable complement to conventional primary amine protecting agents.
Guan, Qi,Jiang, Mingyang,Wu, Junhui,Zhai, Yanpeng,Wu, Yue,Bao, Kai,Zhang, Weige
supporting information
p. 5794 - 5799
(2016/11/06)

Selective Catalytic Hydrogenations of Nitriles, Ketones, and Aldehydes by Well-Defined Manganese Pincer Complexes
Hydrogenations constitute fundamental processes in organic chemistry and allow for atom-efficient and clean functional group transformations. In fact, the selective reduction of nitriles, ketones, and aldehydes with molecular hydrogen permits access to a green synthesis of valuable amines and alcohols. Despite more than a century of developments in homogeneous and heterogeneous catalysis, efforts toward the creation of new useful and broadly applicable catalyst systems are ongoing. Recently, Earth-abundant metals have attracted significant interest in this area. In the present study, we describe for the first time specific molecular-defined manganese complexes that allow for the hydrogenation of various polar functional groups. Under optimal conditions, we achieve good functional group tolerance, and industrially important substrates, e.g., for the flavor and fragrance industry, are selectively reduced.
Elangovan, Saravanakumar,Topf, Christoph,Fischer, Steffen,Jiao, Haijun,Spannenberg, Anke,Baumann, Wolfgang,Ludwig, Ralf,Junge, Kathrin,Beller, Matthias
supporting information
p. 8809 - 8814
(2016/07/29)

Boron-Catalyzed Silylative Reduction of Nitriles in Accessing Primary Amines and Imines
Silylative reduction of nitriles was studied under transition metal-free conditions by using B(C6F5)3 as a catalyst with hydrosilanes as a reductant. Alkyl and (hetero)aryl nitriles were efficiently converted to primary amines or imines under mild conditions. The choice of silanes was found to determine the selectivity: while a full reduction of nitriles was highly facile, the use of sterically bulky silanes allowed for the partial reduction leading to N-silylimines.
Gandhamsetty, Narasimhulu,Jeong, Jinseong,Park, Juhyeon,Park, Sehoon,Chang, Sukbok
p. 7281 - 7287
(2015/07/28)

Hydrogenation of Aliphatic and Aromatic Nitriles Using a Defined Ruthenium PNP Pincer Catalyst
Selective catalytic reductions of nitriles are presented using the commercially available Ru-Macho-BH complex. A variety of aliphatic, aromatic and (hetero)cyclic nitriles including industrially important adipodinitrile are hydrogenated to the corresponding primary amines. Modelling suggests the reaction follows an outer sphere hydrogenation mechanism. An efficient and selective catalytic reduction of nitriles is presented using the commercially available Ru-Macho-BH complex. A variety of aliphatic, aromatic and (hetero)cyclic nitriles including the industrially important adipodinitrile are hydrogenated to the corresponding primary amines. The reaction follows an outer-sphere mechanism.
Neumann, Jacob,Bornschein, Christoph,Jiao, Haijun,Junge, Kathrin,Beller, Matthias
supporting information
p. 5944 - 5948
(2015/09/22)

Straightforward access to cyclic amines by dinitriles reduction
1,1,3,3-Tetramethyldisiloxane (TMDS) and polymethylhydrosiloxane (PMHS), when associated with titanium(IV) isopropoxide, provide two convenient systems for the reduction of nitriles into the corresponding primary amines. Kinetics of the two systems have been studied by 1H NMR and demonstrated that reduction with PMHS occurs faster than with TMDS. These two titanium-based systems reduce both aromatic and aliphatic nitriles in the presence of Br, CC, NO2, OH, and cyclopropyl-ring. In the case of cyclopropyl-nitriles, the formation of secondary amines, which come from an intermolecular reductive alkylation reaction was observed. This result was exploited for the reduction of dinitriles, which led, in one-step, to azepane, piperidine, pyrrolidine, and azetidine derivatives through an intramolecular reductive alkylation reaction.
Laval, Stéphane,Dayoub, Wissam,Pehlivan, Leyla,Métay, Estelle,Favre-Reguillon, Alain,Delbrayelle, Dominique,Mignani, Gérard,Lemaire, Marc
supporting information
p. 975 - 983
(2014/01/23)

CD4-MIMETIC INHIBITORS OF HIV-1 ENTRY AND METHODS OF USE THEREOF
Described herein are small-molecule mimics of CD4, which both enter the Phe43 cavity and target Asp368 of gpl20, the HIV-1 envelope protein. Also described herein are methods of using these compounds to inhibit the transmission or progression of HIV infection. These compounds exhibit antiviral potency greater than that of a known antiviral, NBD-556, with 100% breadth against clade B and C viruses. Importantly, the compounds do not activate HIV infection of CD4-negative, CCR5-positive cells, in contrast to NBD- 556.
-
(2013/07/05)

A practical procedure for reduction of primary, secondary and tertiary amides to amines
A mild and general procedure for reduction of primary, secondary, and tertiary amides using catalytic triruthenium dodecacarbonyl and 1,1,3,3-tetramethyldisiloxane as reductant is described. The reaction is tolerant of numerous functional groups, and the amine products can often be isolated by direct crystallization as hydrochloride salts. The catalyst and silane are commercially available, air stable, and inexpensive, making the procedure accessible for both laboratory and large-scale applications. Copyright
Reeves, Jonathan T.,Tan, Zhulin,Marsini, Maurice A.,Han, Zhengxu S.,Xu, Yibo,Reeves, Diana C.,Lee, Heewon,Lu, Bruce Z.,Senanayake, Chris H.
supporting information
p. 47 - 52
(2013/03/13)

Synthesis of aromatic α-aminoesters: Palladium-catalyzed long-range arylation of primary Csp3-H bonds
Remote control: The title reaction for β-Iζ arylation of α-amino esters with aryl bromides is described. This reaction, which occurs selectively at the terminal position of linear alkyl chains, gives rise to synthetically useful (hetero)arylalanines and homologues after debenzylation (see scheme). Copyright
Aspin, Sam,Goutierre, Anne-Sophie,Larini, Paolo,Jazzar, Rodolphe,Baudoin, Olivier
supporting information
p. 10808 - 10811
(2013/01/15)

A novel efficient and chemoselective method for the reduction of nitriles using the system silane/oxo-rhenium complexes
This work reports the reduction of nitriles to the corresponding primary amines with silanes catalyzed by oxo-rhenium complexes. The catalytic system PhSiH3/ReIO2(PPh3)2 (10 mol %) reduced efficiently a series of nitriles in the presence of a wide range of functional groups such as -Cl, -F, -Br, -I, -CF3, -OCH3, -SCH3, -SO2CH3 and -NHTs.
Cabrita, Ivania,Fernandes, Ana C.
experimental part
p. 8183 - 8186
(2011/10/31)

A mild and efficient method for the reduction of nitriles
A simple and useful method for the reduction of nitriles into the corresponding amines using a tetramethyldisiloxane/titanium(IV) isopropoxide reducing system is described. The synthetic approach is straightforward and provides primary amines as hydrochloride salt in almost quantitative yield. Other advantages of this method, such as easy-to-handle hydride source, inert by-products, that is, TiO2 and oligomeric siloxanes, make it very attractive to prepare primary amines.
Laval, Stéphane,Dayoub, Wissam,Favre-Reguillon, Alain,Berthod, Mika?l,Demonchaux, Patrice,Mignani, Gérard,Lemaire, Marc
experimental part
p. 7005 - 7007
(2010/02/28)

Versatile Reagent for Reduction of Azides to Amines
Triphenylphosphine (TPP) in refluxing methanol effectively reduces a variety of azides 1a-k to amines 2a-k in very good yields.
Pal, Bikash,Jaisankar, Parasuraman,Giri, Venkatachalam S.
p. 1317 - 1323
(2007/10/03)

Preparation of halogenated primary amines
A method of preparing a halogenated primary amine comprising hydrogenating a halogenated oxime in the presence of a catalyst comprising a non-palladium noble metal or a base metal under conditions sufficient to produce a halogenated primary amine.
-
Example 1

(2008/06/13)

Substituent effects. 14. Anomalous dissociation constants in water-organic solvent mixtures: benzylammonium ions and related systems
Thermodynamic dissociation constants in various water-organic solvent mixtures are given for benzylammonium, benzyldialkylammonium, and (2-phenylethyl)ammonium ions.Deviations from the Hammett equation (Eqn. 1) are similar to those observed for carboxylic acids, but of opposite sign.The extended Hammett equation (Eqn. 3), containing the hydrophobic constant, ?, yields good correlations.Derived secondary normal sigma values are exemplified.
Hoefnagel, A. J.,Vos, R. H. de,Wepster, B. M.
p. 22 - 28
(2007/10/02)