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Updated: Aug 26, 2025
Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Photoinduced Three-Component Carboarylation of Unactivated Alkenes with Protic C(sp3)-H Feedstocks
Yang Hong1, Meng-Yuan Dong1, Dong-Sheng Li1
1Jiangsu Key Laboratory of Pesticide Science, College of Sciences, Nanjing Agricultural University, Nanjing 210095, People's Republic of China.
Abstract:
A general and mild strategy involving three-component carboarylation of unactivated alkenes with protic C(sp3)-H feedstocks via photoredox catalysis was reported. This catalytic system is compatible with a broad range of unactivated alkenes, cyano-substituted arenes, and diverse protic C(sp3)-H feedstocks. The synthetic value of this protocol was demonstrated by the late-stage functionalization of complex molecules and the synthesis of the antiallergies including pheniramine, chlorpheniramine, and brompheniramine.
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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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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.