Related Experiment Video
Updated: Dec 5, 2025
12:27
Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
11.2K
Cyanosilylation by Compounds with Main-Group Elements: An Odyssey
Sanjukta Pahar1,2, Gargi Kundu1,2, Sakya S Sen1,2
1Inorganic Chemistry and Catalysis Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pashan, Pune 411008, India.
ACS Omega
|October 19, 2020
Summary
Main-group elements are increasingly used in cyanosilylation catalysis, offering a cost-effective alternative to transition metals. This review explores their mechanisms and development, highlighting advancements in heavier main-group chemistry.
Area of Science:
- Main-group chemistry
- Organometallic catalysis
- Cyanosilylation reactions
Background:
- Significant progress in the structural and reaction chemistry of heavier main-group elements.
- Growing interest in utilizing main-group compounds for catalysis due to cost and abundance.
- Transition metals have historically dominated cyanosilylation, but main-group alternatives are emerging.
Purpose of the Study:
- To provide a comprehensive survey of the state-of-the-art in cyanosilylation methodology using heavier main-group elements.
- To highlight the expansion of main-group elements (e.g., aluminum, silicon, calcium) in this field.
- To compare the reaction mechanisms of main-group catalyzed cyanosilylation with those of transition metals.
Main Methods:
- Literature review and synthesis of recent advancements in main-group catalyzed cyanosilylation.
- Analysis of structural and reaction chemistry data for relevant main-group compounds.
- Comparative mechanistic study of main-group versus transition metal catalyzed cyanosilylation.
Main Results:
- The field of cyanosilylation has expanded beyond transition metals to include a wide range of main-group elements.
- Main-group elements like aluminum, silicon, and calcium are now actively employed in cyanosilylation reactions.
- Distinct mechanistic pathways are observed for cyanosilylation reactions catalyzed by main-group compounds compared to transition metals.
Conclusions:
- Main-group element compounds represent a viable and developing alternative to transition metals for cyanosilylation catalysis.
- The exploration of heavier main-group elements in catalysis is a rapidly advancing area.
- Understanding the mechanistic differences is key to further developing main-group catalyzed cyanosilylation.
Related Concept Videos
01:32Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview
3.6K
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...
3.6K
01:20Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
2.2K
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...
2.2K
01:23Properties of Organometallic Compounds
1.4K
Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.
1.4K
01:10Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism
3.9K
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...
3.9K
02:26Preparation and Reactions of Sulfides
5.5K
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.
5.5K
01:12Preparation of Nitriles
2.4K
One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
2.4K