Ionic‐Liquid‐Influenced Expeditious and Stereoselective Synthesis of Olefins

Bhilare, Sachin V.; Darvatkar, Nitin B.; Deorukhkar, Amol R.; Rasalkar, Meghana S.; Salunkhe, Manikrao M.

doi:10.1080/00397910701544794

Cited by 7 publications

(5 citation statements)

References 13 publications

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“…By contrast, the homocoupling of aromatic aldehydes using the ionic liquid, 1-butyl-3-methylimidazolium chloroaluminate [ zinc exhibits preferential formation of (Z)-stilbenes (Scheme 8), 46 although the reasons for this are not clear. …”

Section: Stereochemistrymentioning

confidence: 96%

“…92 Zinc dust in combination with the acidic ionic liquid 1-butyl-3-methylimidazolium chloroaluminate converts aromatic aldehydes and ketones to alkenes with (Z)-stereoselectivity. 46 Zirconium Reagents. Similarly to titanium, the low-valent zirconium reagent generated by the reduction of ZrCl 4 with lithium reacts with aromatic aldehydes and ketones to produce alkenes with (E)-stereoselectivity.…”

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confidence: 99%

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The McMurry Coupling and Related Reactions

Takeda

Tsubouchi

2013

Organic Reactions

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The McMurry coupling reaction has been recognized as one of the most efficient methods for the synthesis of alkenes from carbonyl compounds. This reaction can be applied to the preparation of various alkenes that are otherwise difficult to prepare. For example, sterically congested tetrasubstituted alkenes as well as medium to large membered rings involving natural products may be accessed via this process. This coupling utilizes various low‐valent titanium reagents generated by the reduction of titanium (III or IV) chloride with K, Zn, LiAlH 4 , C 8 K, amongst others. Furthermore, a variety of low‐valent metal species other than titanium, including aluminum, zirconium, niobium, molybdenum, indium, tungsten, and samarium, have also been found to promote the reductive coupling of carbonyl compounds. The scope and limitations of these reagent systems are reviewed in this chapter, together with the stereochemistry and reaction mechanism. This reaction is categorized into four coupling modes: i) homocoupling giving symmetrical alkenes, ii) mixed coupling giving unsymmetrical alkenes, iii) intramolecular coupling giving cycloalkenes, and iv) tandem coupling giving cyclic polyenes. Characteristics of these reaction modes are described briefly. A selection of synthetic applications are reviewed, including examples of the preparation of sterically congested and strained alkenes, medium to large‐ring compounds, biologically active targets, as well as substrates applicable in material science. Experimental conditions used for this versatile process are summarized to assist the choice of suitable conditions.

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Section: Stereochemistrymentioning

confidence: 96%

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confidence: 99%

The McMurry Coupling and Related Reactions

Takeda

Tsubouchi

2013

Organic Reactions

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“…The dual functionality of ILs in the "classic" form, where the IL plays both the role of solvent and the catalyst, has been well described in the literature. [32][33][34][35][36][37] An interesting example of the dual functionality of ILs was reported by Alizadeh. 38 In the condensation of aromatic carbonyl compounds with nitroalkanes, 2-hydroxyethylammonium formate IL was used.…”

Section: Introductionmentioning

confidence: 98%

Dual functionality of amphiphilic 1-alkyl-3-methylimidazolium hydrogen sulfate ionic liquids: surfactants with catalytic function

2016

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“…On the other hand, solubilizing properties of functionalized ionic liquids in combination with their surface and catalytic properties can be a very promising alternative for the classical two‐phase catalysis, being similar to common phase transfer catalysis [12–14] . One of the features that distinguishes ionic liquids from other common solvents is their polyfunctionality in various aspects [15–18] …”

Section: Introductionmentioning

confidence: 99%

“…[12][13][14] One of the features that distinguishes ionic liquids from other common solvents is their polyfunctionality in various aspects. [15][16][17][18] The literature describes many examples of the use of ionic liquids in epoxidation reactions. They are most often used as components of catalyst systems based on "oxidizing" metals such as W, Re and Mn.…”

Section: Introductionmentioning

confidence: 99%

Epoxidation of unsaturated fatty acid ester promoted by imidazolium acidic ionic liquids: An unexpected selectivity phenomena

2022

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Epoxidation of linseed oil fatty acid ethyl esters promoted by a series of functionalized imidazolium ionic liquids was studied. In this reaction acidic imidazolium ILs behave not only as an acid catalysts but also play an additional role as a specific activator for the reaction of epoxidation of unsaturated fatty derivatives in H 2 O 2 /formic acid oxidation system. The obtained results indicate that the hydrogen-bonding interaction of imidazolium cation with epoxide group influences the selectivity of the epoxidation reaction. In particular, the presence of unprotected weak "acid" C2-H proton significantly lowers the selectivity to hydroxyl derivatives. The obtained results also point to another example of specific polyfunctionality of ILs, especially imidazolium one, used as surfactants and process activators.

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Ionic‐Liquid‐Influenced Expeditious and Stereoselective Synthesis of Olefins

Cited by 7 publications

References 13 publications

The McMurry Coupling and Related Reactions

The McMurry Coupling and Related Reactions

Dual functionality of amphiphilic 1-alkyl-3-methylimidazolium hydrogen sulfate ionic liquids: surfactants with catalytic function

Epoxidation of unsaturated fatty acid ester promoted by imidazolium acidic ionic liquids: An unexpected selectivity phenomena

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