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Updated: Oct 29, 2026
Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
Published on: November 21, 2017
Zinc-Catalyzed Dehydrogenative Alkynylation of BN-Polycyclic Aromatics
Anran Zhang1, Qibin Wang2, Qiang Deng1
1Key Laboratory of Catalysis and Energy Materials Chemistry of Ministry of Education and Hubei Key Laboratory of Catalysis and Materials Science, School of Chemistry and Materials Science, South-Central Minzu University, Wuhan, P. R. China.
Abstract:
We report a zinc-catalyzed dehydrogenative alkynylation of BN-polycyclic aromatics with terminal alkynes, enabling efficient access to BN-embedded phenylacetylene scaffolds via direct B─H/C─H coupling. This transformation proceeds under mild conditions with broad substrate scope, accommodating diverse BN-polycyclic aromatics and aryl, heteroaryl, and alkyl alkynes, as well as functionally complex substrates, with excellent functional group tolerance. The method is scalable and enables facile downstream derivatization. Photophysical studies reveal tunable absorption and emission properties governed by π-extension and BN incorporation, distinct from all-carbon analogues. Mechanistic studies support a pathway involving alkynyl-zinc intermediates and rate-determining B─H activation, accompanied by H2 evolution. This work provides a general and efficient strategy for constructing BN-containing π-conjugated systems with potential in functional materials and molecular design.
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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.
02:34Preparation of Alkynes: Dehydrohalogenation
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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.
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