13605-95-3Relevant academic research and scientific papers
Reductive amination of carboxylic acids and [11C]magnesium halide carboxylates
Perrio-Huard, Cecile,Aubert, Catherine,Lasne, Marie-Claire
, p. 311 - 316 (2000)
The reductive amination of carboxylic acids was shown to be promoted by 2-chloropyridine hydrochloride (3 eq). It allowed the one-pot preparation of N-alkylamines in yields up to 93% from carboxylic acid (1 eq), amine (1 eq) and sodium borohydride (5 molar eq). The reaction, carried out with [11C]magnesium halide carboxylates (11C, β+, t1/2:20 min), led to N-[11C]alkylamines in 20-25% radiochemical yields (decay corrected to the end of bombardment, 30 min preparation time from [11C]CO2). In this case, the addition of pyridinium salts led only to the corresponding [11C]carboxylic acids.
Solid-phase synthesis on functionalised fluoropolymer resins. Part 1: Nafion resin sulfonamide-immobilised carboxylic acid derivatives and aryl vinyl sulfones
Akhtar, Mahmoud,Kroll, Friedrich E.K.,Gani, David
, p. 4487 - 4491 (2000)
The preparation and properties of Nafion resin sulfonamide systems derived from methyl glycinate and from 3-hydroxyethylaniline are described. Nafion derivatisation reactions were slow and maximum achievable functionalisations were 50% of the ion exchange
Catalyst-free multi-component cascade C-H-functionalization in water using molecular oxygen: An approach to 1,3-oxazines
Deb, Mohit L.,Pegu, Choitanya D.,Borpatra, Paran J.,Saikia, Prakash J.,Baruah, Pranjal K.
, p. 4036 - 4042 (2017)
Herein, catalyst-free 3-component reactions of naphthols, aldehydes, and tetrahydroisoquinolines to synthesize 1,3-oxazines is reported. The reaction is performed in H2O in the presence of O2 as the sole oxidant at 100 °C, which proceeds through the formation of 1-aminoalkyl-2-naphthols followed by selective α-C-H functionalization of tert-amine.
USE OF N-CHELATING RUTHENIUM COMPLEXES IN THE METATHESIS REACTION
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Paragraph 0083-0087, (2021/08/07)
The subject matter of the invention is the use of a ruthenium complex of the formula 1, wherein the individual substituents have meanings as indicated in the olefin metathesis reactions description, including a reaction selected from such as ring-closing
N?N Bond Formation Using an Iodonitrene as an Umpolung of Ammonia: Straightforward and Chemoselective Synthesis of Hydrazinium Salts
Tota, Arianna,Colella, Marco,Carlucci, Claudia,Aramini, Andrea,Clarkson, Guy,Degennaro, Leonardo,Bull, James A.,Luisi, Renzo
supporting information, p. 194 - 199 (2020/10/28)
The formation of hydrazinium salts by N?N bond formation has typically involved the use of hazardous and difficult to handle reagents. Here, mild and operationally simple conditions for the synthesis of hydrazinium salts are reported. Electrophilic nitrogen transfer to the nitrogen atom of tertiary amines is achieved using iodosylbenzene as oxidant and ammonium carbamate as the N-source. The resulting process is highly chemoselective and tolerant to other functional groups. A wide scope is reported, including examples with bioactive molecules. Insights on the structure of hydrazinium salts were provided by X-ray analysis. (Figure presented.).
Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations
Liu, Shuyang,Tian, Miao,Bu, Xiubin,Tian, Hua,Yang, Xiaobo
supporting information, p. 7738 - 7744 (2021/05/07)
Photoactive two-dimensional covalent organic frameworks (2D-COFs) have become promising heterogenous photocatalysts in visible-light-driven organic transformations. Herein, a visible-light-driven selective aerobic oxidation of various small organic molecules by using 2D-COFs as the photocatalyst was developed. In this protocol, due to the remarkable photocatalytic capability of hydrazone-based 2D-COF-1 on molecular oxygen activation, a wide range of amides, quinolones, heterocyclic compounds, and sulfoxides were obtained with high efficiency and excellent functional group tolerance under very mild reaction conditions. Furthermore, benefiting from the inherent advantage of heterogenous photocatalysis, prominent sustainability and easy photocatalyst recyclability, a drug molecule (modafinil) and an oxidized mustard gas simulant (2-chloroethyl ethyl sulfoxide) were selectively and easily obtained in scale-up reactions. Mechanistic investigations were conducted using radical quenching experiments and in situ ESR spectroscopy, all corroborating the proposed role of 2D-COF-1 in photocatalytic cycle.
Co(iii)-catalysed regioselective linear C(8)-H olefination of isoquinolone with terminal aromatic and aliphatic alkynes
Chandra, Devesh,Gupta, Puneet,Kumar, Nikunj,Parmar, Diksha,Sharma, Upendra,Sumit
supporting information, p. 11613 - 11616 (2021/11/12)
A regioselective C8 linear olefination of isoquinoline-1H-2-one with terminal (aromatic and aliphatic) alkynes is reported under Co(iii) catalysis. This is an exclusive report on the C8 functionalization of isoquinolone using non-noble transition metal co
Iron-Catalyzed Oxidative Amination of Benzylic C(sp3)–H Bonds with Anilines
Song, Yan-Ling,Li, Bei,Xie, Zhen-Biao,Wang, Dan,Sun, Hong-Mei
, p. 17975 - 17985 (2021/12/13)
Iron-catalyzed oxidative amination of benzylic C(sp3)–H bonds with anilines bearing electron-withdrawing groups (EWGs) or electron-donating groups (EDGs) is realized based on simple variations of N-substituents on imidazolium cations in novel ionic Fe(III) complexes. The structural modification of the imidazolium cation resulted in regulation of the redox potential and the catalytic performance of the iron metal center. Using DTBP as oxidant, [HItBu][FeBr4] showed the highest catalytic activity for anilines bearing EWGs, while [HIPym][FeBr4] was more efficient for EDG-substituted anilines. This work provides alternative access to benzylamines with the advantages of both a wide substrate scope and iron catalysis.
BF3·Et2O as a metal-free catalyst for direct reductive amination of aldehydes with amines using formic acid as a reductant
Fan, Qing-Hua,Liu, Xintong,Luo, Zhenli,Pan, Yixiao,Xu, Lijin,Yang, Ji,Yao, Zhen,Zhang, Xin
supporting information, p. 5205 - 5211 (2021/07/29)
A versatile metal- and base-free direct reductive amination of aldehydes with amines using formic acid as a reductant under the catalysis of inexpensive BF3·Et2O has been developed. A wide range of primary and secondary amines and diversely substituted aldehydes are compatible with this transformation, allowing facile access to various secondary and tertiary amines in high yields with wide functional group tolerance. Moreover, the method is convenient for the late-stage functionalization of bioactive compounds and preparation of commercialized drug molecules and biologically relevant N-heterocycles. The procedure has the advantages of simple operation and workup and easy scale-up, and does not require dry conditions, an inert atmosphere or a water scavenger. Mechanistic studies reveal the involvement of imine activation by BF3and hydride transfer from formic acid.
Photocatalyst- And transition-metal-free α-allylation of: N -aryl tetrahydroisoquinolines mediated by visible light
Li, Zhuohua,Ma, Pengju,Tan, Yongzhu,Liu, Yufei,Gao, Min,Zhang, Yujun,Yang, Bo,Huang, Xuan,Gao, Yuan,Zhang, Junmin
supporting information, p. 646 - 650 (2020/02/21)
A convenient and efficient α-allylation of N-aryl tetrahydroisoquinolines has been achieved. This transformation can be realized under only visible light irradiation without the aid of transition metals or photocatalysts. The mechanism involves a novel in situ-generated electron-donor-acceptor (EDA) complex between the N-aryl tetrahydroisoquinolines and an allyl or a benzyl bromide. Irradiation with purple light triggered single-electron transfer (SET) from the N-aryl tetrahydroisoquinolines to the allyl or benzyl bromide of the EDA complex, inducing the formation of the corresponding allyl or benzyl radical and the subsequent radical-radical coupling. This approach represents the first example of a photocatalyst- and transition-metal-free α-allylic and benzylic functionalization of N-aryl tetrahydroisoquinolines.
