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Fe-Catalysed Coupling Reactions Between Alkynes and Alcohols
Siddique Khan1, Beeraiah Baire1
1Department of Chemistry, Indian Institute of Technology Madras, Chennai, 600036, India.
Iron catalysis enables efficient synthesis of C-O bonds by coupling alkynes and alcohols. This green chemistry approach offers high atom economy and uses abundant, low-toxicity materials.
Area of Science:
- Organic Chemistry
- Catalysis
- Green Chemistry
Background:
- Iron catalysis is an emerging field in organic synthesis.
- Traditional methods for C-O bond formation often involve toxic reagents or harsh conditions.
Purpose of the Study:
- To review synthetic developments in iron-catalyzed coupling of alkynes and alcohols for C-O bond formation.
- To highlight the adherence of these methods to Green Chemistry principles.
Main Methods:
- Literature review of iron-catalyzed reactions from 2008-2020.
- Analysis of reaction mechanisms, atom economy, and byproduct formation.
Main Results:
- Iron catalysis provides highly atom-economic (up to 100%) routes to C-O bonds.
- These reactions generate only water as a byproduct, aligning with Green Chemistry.
- Utilizes abundant, low-toxicity alcohols, reducing pre-functionalization steps.
Conclusions:
- Iron-catalyzed coupling of alkynes and alcohols is a sustainable and efficient synthetic strategy.
- The field shows significant promise for developing novel reactions in organic synthesis.
- This review serves as a valuable resource for researchers in synthetic chemistry.
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Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
02:47Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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