185456-43-3Relevant academic research and scientific papers
Facile synthesis of mono-, di-, and trisubstituted alpha-unbranched hydrazines
Rasmussen, Lars K.
, p. 3627 - 3629 (2006)
Methods for the alkylation of di-tert-butyl hydrazine-1,2-dicarboxylate were investigated. It was found that under mild conditions mono- or di-substituted hydrazine derivatives were obtained in good to excellent yield. Furthermore, it was shown that one o
Electrophilic amination of organozinc halides
Velarde-Ortiz, Raffet,Guijarro, Albert,Rieke, Reuben D.
, p. 9157 - 9160 (1998)
The reaction of several functionalized primary, secondary and tertiary organozinc bromides, benzylzinc bromide, functionalized arylzinc halides and one heteroarylzinc bromide with ditert-butyl azodicarboxylate is described. The reaction products, N,N'-dit
Convenient C(sp3)-H bond functionalisation of light alkanes and other compounds by iron photocatalysis
Duan, Chunying,Jin, Yunhe,Meng, Changgong,Wang, Lifang,Wang, Xinyao,Zhang, Qingqing
supporting information, p. 6984 - 6989 (2021/09/28)
Light alkanes are natural organic carbon sources and widely distributed in nature. Transforming them into value-added fine chemicals affords attractively economic and ecological benefits as well as enormous chemical challenges. Herein, we report a practical iron-catalysed photoredox system for C(sp3)-H transformation of ethane, propane, and other light alkanes to C-N and C-C bonds under ambient temperature. The present method with abundant and inexpensive iron salts as photocatalysts exhibits high catalytic efficiency (turnover number up to 8000), mild conditions, and the convenience of being purified and scaled up without chromatography. A photo-induced ligand-to-metal charge transfer between Fe(iii) and Cl- generates a highly active chlorine radical that sequentially acts as hydrogen atom transfer catalyst. Therefore, the sustainable, convenient, and environmentally friendly system will find wide applications in high-value-added transformation of natural alkanes with novel inspiration not only for organic synthesis, but also for designing catalytically active organic/inorganic materials. This journal is
Copper-Catalyzed Aerobic Oxidative Cleavage of Unstrained Carbon-Carbon Bonds of 1,1-Disubstituted Alkenes with Sulfonyl Hydrazides
Yi, Dong,He, Linying,Qi, Zhongyu,Zhang, Zhijie,Li, Mengshun,Lu, Ji,Wei, Jun,Du, Xi,Fu, Qiang,Wei, Siping
supporting information, p. 859 - 865 (2021/03/04)
Alkoxy radical-mediated carbon-carbon bond cleavages have emerged as a powerful strategy to complement traditional ionic-type transformations. However, carbon-carbon cleavage reaction triggered by alkoxy radical intermediate derived from the combination of alkyl radical and dioxygen, is scarce and underdeveloped. Herein, we report alkoxy radical, which was generated from alkyl radical and dioxygen, mediated selective cleavage of unstrained carbon-carbon bond for the oxysulfonylation of 1,1-disubstituted alkenes, providing facile access to a variety of valuable β-keto sulfones. Mechanistic experiments indicated alkoxy radical intermediate that underwent subsequent regioselective β-scission might be involved in the reaction and preliminary computational studies were conducted to provide a detailed explanation on the regioselectivity of the C—C bond cleavage. Notably, the strategy was successfully applied for constructing uneasily obtained architecturally intriguing molecules.
Method for synthesizing nitrogen-containing aromatic compound through one-step photocatalytic lignin depolymerization and amination (by machine translation)
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Paragraph 0027-0032; 0045-0050, (2019/09/13)
The invention discloses a method, synthesizing a nitrogen-containing aromatic compound through one-step photocatalytic lignin depolymerization and amination. Belong to lignin application technical field. To the invention, lignin or a model compound thereof is dissolved in a solvent, and under the excitation, photo-catalyst catalysis, the auxiliary and nitrogen source react 6~24 hours at room temperature, C-C bond is selectively cracked and aminated to synthesize nitrogen-containing aromatic compound; lignin or a model compound, photocatalyst, auxiliary, nitrogen source molar ratio 100: (1~20): (1~100): 100. The C-C bond disclosed by the invention is simple, mild, high, selective and high, 100% and can continuously feed, has a good degradation effect on natural lignin, and can further react with the hydrazine product to obtain the nitrogen heterocyclic compound, and the like, and has the advantages. (by machine translation)
Alkylation Reactions of Azodicarboxylate Esters with 4-Alkyl-1,4-Dihydropyridines under Catalyst-Free Conditions
Nakajima, Kazunari,Zhang, Yulin,Nishibayashi, Yoshiaki
supporting information, p. 4642 - 4645 (2019/06/17)
Introduction of alkyl groups on azodicarboxylate esters is an important method to prepare alkyl amine derivatives. Herein, we report reactions of 4-alkyl-1,4-dihydropyridines as alkylation reagents with di-tert-butyl azodicarboxylate to prepare alkyl amin
Synthesis of benzyl hydrazine derivatives: Via amination of benzylic C(sp3)-H bonds with dialkyl azodicarboxylates
Samzadeh-Kermani
, p. 4766 - 4772 (2018/03/21)
A novel synthesis of benzyl hydrazines through oxidative amination of benzylic C-H bonds has been developed. The resulting aminated products are accessed directly from the reaction of alkylarenes with dialkyl/diphenyl azodicarboxylates using Cu2O/Phen as the catalytic system. The reaction proceeded smoothly and a decent range of N-substituted hydrazides was synthesized in acceptable to good yields. Both primary and secondary sp3 C-H sources afford only monoamination products.
Convenient synthesis of monobenzylated hydrazides via aqueous zinc-mediated addition reactions
Breton, Gary W.
, p. 1128 - 1136 (2014/04/03)
Addition of substituted benzyl bromides to dialkyl azodicarboxylates under aqueous zinc-mediated addition conditions occurs readily to afford monobenzylated hydrazides in good to excellent yields. The reaction is tolerant of a variety of substituents on the benzyl bromide ring. Several dialkyl azodicarboxylates were successfully tested under the reaction conditions. The limitations of the reaction are also addressed.
Effective strategy for the systematic synthesis of hydrazine derivatives
Bredihhin, Aleksei,M?eorg, Uno
, p. 6788 - 6793 (2008/12/20)
A new and efficient strategy for the systematic synthesis of hydrazine derivatives is reported. It allows the synthesis of up to tetrasubstituted hydrazine derivatives with minimal number of steps using only one protecting group or without any of them at all. Simple and readily available starting materials such as hydrazine hydrate or phenylhydrazine can be used. A variety of substrates were used to investigate scope and limitations of this strategy, additionally one full synthetic sequence was performed.
Preparation of Multiply Protected Alkylhydrazine Derivatives by Mitsunobu and PTC Approaches
Brosse, Nicolas,Pinto, Maria-Fatima,Jamart-Gregoire, Brigitte
, p. 4757 - 4764 (2007/10/03)
Alkylation reactions of hydrazine derivatives by Mitsunobu or PTC approaches are described. It has been shown that aminophthalimide derivatives are better acidic partners than their aminoimidodicarbonate (NBoc2) analogues, the presence of the phthaloyl group increasing the acidity of the sole proton and concomitantly reducing steric hindrance. Moreover, N-aminophthalimide derivatives can be efficiently converted into the corresponding N-amino-imidodicarbonates by a three-stage, one-flask procedure under very mild conditions. These procedures can also be efficiently used for the preparation of orthogonally Nα,Nβ -diprotected α-hydrazino esters. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).
