Acid ionic liquid promoted addition of C(sp3)–H bond to aldehyde

Zhang, Xueyan; Dong, Dao‐Qing; Yue, Tao; Hao, Shu; Wang, Zu‐Li

doi:10.1016/j.tetlet.2014.08.034

Cited by 25 publications

(3 citation statements)

References 55 publications

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“…Ionic liquids (ILs) are composed of cations and anions with melting points around or below ambient temperature . ILs have been investigated as potential media for methane transformation, − storage, − and separation − owning to their unique properties, such as negligible vapor pressure, weak coordination, and good solubility. A number of ionic liquids based on imidazolium, − ,,− phosphonium, − and ammonium have been reported for their high methane solubility.…”

Section: Introductionmentioning

confidence: 99%

Structural Dependence and Spectroscopic Evidence of Methane Dissolution in Ionic Liquids

Huang

Yan

et al. 2018

J. Phys. Chem. B

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High methane dissolution capacity in a liquid is important for methane storage and transformation. In this work, methane solubility in different ionic liquids (ILs) was studied and was found associated with IL's structural and physical properties. In imidazolium-based ILs, ILs containing C-F and long alkyl chain showed high methane solubility mainly due to lower surface tension and molar density. Reducing the surface tension of solvent by adding 0.16 mol of trimethyl-1-propanaminium iodide (FC-134) with respect to [Bmim][NTf] increased methane solubility by 39.3%. In situ high-pressure attenuated total reflection Fourier transform infrared spectroscopic results indicated a reversible process of methane dissolution in the ILs. The antisymmetric C-H stretching band of dissolved methane in ILs showed highly prominent rotational-vibrational bands with high intensity and narrow half-peak width compared to gaseous methane. Induced interaction between methane and IL resulted in increased dipole variation strength and reduced methane molecular symmetry. The constant antisymmetric C-H stretching peak at 3016.85 cm revealed an unconstrained methane rotation in the stable physical and chemical environment of IL. Methane insertion into the IL's intranetwork space needs activation energy to overcome the interaction of cation-anion network. Kinetic analysis of methane in [Bmim][NTf] and [Bmim][HSO] at different temperatures indicated that methane dissolution in these two ILs was a reversible first-order and very weak endothermic process and that methane dissolution required high activation energy in ILs with stronger cation-anion interaction.

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Section: Introductionmentioning

confidence: 99%

Structural Dependence and Spectroscopic Evidence of Methane Dissolution in Ionic Liquids

Huang

Yan

et al. 2018

J. Phys. Chem. B

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“…After the microwave promoted alkylation of aldehydes with 2‐methyl azaarenes (Scheme ), another method for this alkylation was developed in acidic‐ionic liquid at 100 °C (Scheme ). These conditions were extended to make a total of 21 alcohols 23 with yields ranging from 65 to 95 %.…”

Section: Alkylationmentioning

confidence: 99%

C(sp³)‐H Functionalization of 2‐Methyl Azaarenes: Highly Facile Approach to Aza‐Heterocyclic Compounds

Latha

Yaragorla

2020

Eur J Org Chem

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Quinolines and their derivatives have always been promising leads for drug discovery, material applications and designing new catalysts. In the past decade, C(sp 3 )-H functionalization of 2-methyl azaarenes, particularly 2-methyl quinol- [a] ACYLATIONAlmost the early report of C(sp 3 )-H functionalization of 2methyl quinoline was performed by treating with esters using sodamide or potassium amide as the base. This reaction followed the nucleophilic substitution at the sp 2 center of the ester by the benzylic carbanion which was formed by the base treatment (Scheme 2). A total of 15 compounds were made using this method with the yields ranging from 14-62 %. [11] After a couple of years, another report [12] appeared for this transformation, where 2-methyl quinoline and esters were reacted in the presence of phenyllithium to give corresponding acylated quinolines in 36-80 % yields. Later in 1974, J. F. Wolfe reported another approach by treating 2-methyl quinoline with esters refluxed in dimethoxyethane (DME) using sodium hydride for 1-48 h to obtain the corresponding acylated quinolines in 44-98 % yields. [13] Scheme 2. Minireview

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“…141 Wang et al investigated an ionic liquid promoted nucleophilic addition of alkyl azaarenes to aldehydes. 142 Wang et al also studied a series of Lewis-acid-catalyzed nucleophilic reactions of 2-methylazaarenes with aldehydes; 2-(pyridin-2-yl)ethanols with common substituents were formed through the LiNTf 2 promoted aldol reaction, 2-alkenylpyridines were synthesized exclusively in the (E)-form in the presence of LiNTf 2 and H 2 NTf, and 2-alkenylquinolines were obtained by the reaction of 2-methylquinolines and aldehydes using La(Pfb) 3 as the catalyst. 143 Niu and Guo reported tosic acid catalyzed reaction of 2-methyl azaarenes and aromatic aldehydes to give 1,3-di(2-quinolyl)propane Scheme 68 Hou's approach for the addition of azaarenes to olefins.…”

Section: Reactions Of Methylazaarenesmentioning

confidence: 99%

Utilization of methylarenes as versatile building blocks in organic synthesis

2015

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The development of practical and efficient methods for C-C and C-X bond formation has attracted a great deal of current attention with the advent of C-H functionalization reactions. Hydrocarbons are perhaps the most inexpensive and readily available materials, and utilisation of such materials for the synthesis of essential chemicals is virtually and economically pragmatic. The means to utilize easily accessible hydrocarbons not only represents a useful, potent and straightforward alternative, but also constitutes an excellent opportunity to improve our chemical knowledge about a relatively unexplored domain. Early examples using alkylarenes are generally limited to their conversion to aldehydes, carboxylic acids, and nitriles. This review intends to focus on the latest developments adopting modern strategies for sp(3) C-H functionalization of methylarenes to achieve a diverse range of important organic compounds.

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Acid ionic liquid promoted addition of C(sp3)–H bond to aldehyde

Cited by 25 publications

References 55 publications

Structural Dependence and Spectroscopic Evidence of Methane Dissolution in Ionic Liquids

Structural Dependence and Spectroscopic Evidence of Methane Dissolution in Ionic Liquids

C(sp³)‐H Functionalization of 2‐Methyl Azaarenes: Highly Facile Approach to Aza‐Heterocyclic Compounds

Utilization of methylarenes as versatile building blocks in organic synthesis

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Acid ionic liquid promoted addition of C(sp3)–H bond to aldehyde

Cited by 25 publications

References 55 publications

Structural Dependence and Spectroscopic Evidence of Methane Dissolution in Ionic Liquids

Structural Dependence and Spectroscopic Evidence of Methane Dissolution in Ionic Liquids

C(sp3)‐H Functionalization of 2‐Methyl Azaarenes: Highly Facile Approach to Aza‐Heterocyclic Compounds

Utilization of methylarenes as versatile building blocks in organic synthesis

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C(sp³)‐H Functionalization of 2‐Methyl Azaarenes: Highly Facile Approach to Aza‐Heterocyclic Compounds