Related Experiment Video
Updated: Aug 30, 2025
12:27
Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
10.9K
Donor free stibenium cation as an efficient cyanosilylation catalyst.
Nilanjana Sen1, Prachi Gothe1, Pallavi Sarkar2
1Department of Chemistry, Indian Institute of Science Education and Research Pune, Dr Homi Bhabha Road, Pashan, Pune-411008, India. shabana@iiserpune.ac.in.
Chemical Communications (Cambridge, England)
|August 30, 2022
Summary
Novel stibenium cations were synthesized and applied as catalysts for cyanosilylation reactions. Compound 4 demonstrated excellent catalytic activity in the cyanosilylation of aldehydes and ketones, showcasing its potential in organic synthesis.
Area of Science:
- Organometallic Chemistry
- Catalysis
- Synthetic Chemistry
Background:
- Stibenium cations are Lewis acidic species with potential catalytic applications.
- Cyanosilylation of carbonyl compounds is a crucial transformation in organic synthesis.
- Development of efficient catalysts for cyanosilylation remains an active area of research.
Purpose of the Study:
- To synthesize novel stibenium cations.
- To investigate their catalytic activity in the cyanosilylation of carbonyl compounds.
Main Methods:
- Synthesis of chlorostibine L1SbCl.
- Treatment with silver triflate (AgOTf) and silver hexafluoroantimonate (AgSbF6) to form stibenium salts.
- Evaluation of catalytic activity in cyanosilylation reactions of aldehydes and ketones.
Main Results:
- Successful synthesis of donor-free stibenium triflate (L1SbOTf) and stibenium hexafluoroantimonate ([L1Sb]+[SbF6]-).
- Compound 4 ([L1Sb]+[SbF6]-) exhibited excellent catalytic activity in the cyanosilylation of various aldehydes and ketones.
- The catalytic efficiency was superior compared to related compounds.
Conclusions:
- Novel stibenium cations can be effectively synthesized.
- Stibenium salts, particularly [L1Sb]+[SbF6]-, are highly active catalysts for cyanosilylation.
- These findings open new avenues for catalytic applications of stibenium compounds in organic synthesis.
More Related Videos
Related Concept Videos
01:26Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride
1.9K
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
1.9K
01:10Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism
3.3K
Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide anion...
3.3K
02:26Preparation and Reactions of Sulfides
5.1K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
5.1K
01:32Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview
3.0K
Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...
3.0K
02:17Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
3.4K
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
3.4K
01:20Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
2.0K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.0K