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Updated: Jan 10, 2026
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Iron-Catalyzed Alkynylation of Strong Aliphatic C─H Bonds
Qi-Ping Huang1, Lu Cheng1, Linlin Zhao1
1State Key Laboratory of Microbial Technology, Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science, Nanjing Normal University, Wenyuan Road No.1, Nanjing, 210023, China.
Abstract:
The development of synthetic catalysts capable of replicating cytochrome P450's remarkable C─H activation proficiency while suppressing oxygen rebound presents a fundamental challenge in catalysis, yet holds transformative potential for alkane functionalizations. Herein, we report an iron/EtBCMOM (L-cystine-based ligand) catalytic system for the selective distal methylene C(sp3)-H alkynylation of alkanes using alkynyl sulfones. This catalytic paradigm establishes a robust platform for the direct transformation of inert C(sp3)─H bonds into versatile alkyne functionalities, exhibiting exceptional predictability in regioselectivity and accommodating an expansive substrate scope (>60 structurally diverse examples). The technology unlocks previously inaccessible chemical space, enabling single-step derivatization of natural products, medicinally relevant molecules, and commodity feedstocks at traditionally unreactive positions.
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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.
02:27Preparation 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.
02:47Alkynes 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.
02:01Alkynes 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.