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Selective Electrochemical Defluorinative Hydroxymethylation toward Difluoro-Substituted Alcohol Building Blocks
Andrey Shatskiy1, Márk Holczer1, Johannes Winter1
1Department of Chemistry, KTH Royal Institute of Technology, SE-100 44 Stockholm, Sweden.
None:
Difluoromethylated compounds are of high importance for pharmaceutical and agrochemical industries; however, access to these structures remains limited due to the scarcity of reliable synthetic methods for their formation. This work presents a straightforward electrochemical synthesis of difluoromethyl-substituted alcohol building blocks via the selective monodefluorination of trifluoromethyl arenes with concomitant hydroxymethylation. The transformation proceeds with high chemoselectivity for a range of trifluoromethyl arene substrates under mild conditions. Mechanistic studies suggest that the reaction relies on reductive radical-polar crossover to furnish a key carbanion intermediate.
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02:48Conversion of Alcohols to Alkyl Halides
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The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
01:38Preparation of Alcohols via Substitution Reactions
Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group. The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2, depending on the nature of carbon attached to the halide.
Primary alcohols are synthesized from primary alkyl halides, and the...
02:29Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.
02:31Protection of Alcohols
Protection
It defines a protecting group as the masking agent to make the more reactive species inert to a given set of conditions. This concept is depicted via the illustration of liquid flow through different outlets in an assembly of pipes. The analogy helps to understand the role...
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