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Carbosulfonylation of Alkynes: A Direct Conversion of sp-C to sp3-C through Visible Light-Mediated 3-Component
Mandapati Bhargava Reddy1,2, Vanessa E Becker1, Eoghan M McGarrigle1,2
1Centre for Synthesis & Chemical Biology, UCD School of Chemistry, Belfield, Dublin 4, Ireland.
Abstract:
A 3-component metal-free carbosulfonylation of alkynes is reported using readily available alkyl carboxylic acids and arylsulfinates under visible light irradiation. This photochemical approach gives direct conversion of sp-C to sp3-C yielding highly functionalized alkyl sulfones. It employs feedstock chemicals as starting materials and shows a broad substrate scope and moderate diastereoselectivity. The method's utility is highlighted in the synthesis of sedum alkaloids. A single photocatalyst is proposed to be active in two distinct photocatalytic cycles operating in tandem.
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02:24Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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.
02:27Preparation of Alkynes: Alkylation Reaction
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.
02:38Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
02:01Alkynes to Carboxylic Acids: Oxidative Cleavage
02:40Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration
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.