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Acrylamides from alkynes: a synthetic overview
Shivam Bhargav1, Akash Singh1, Ashirwad Divedi1
1Department of Chemistry, Babasaheb Bhimrao Ambedkar University (A Central University) Vidya Vihar, Raebareli Road, Lucknow-226025, Uttar Pradesh, India. jawaharlj@bbau.ac.in.
Abstract:
The transformation of alkynes into nitrogen-containing compounds has emerged as a crucial strategy in modern synthetic chemistry. This review article highlights diverse catalytic approaches for incorporating nitrogen from amines, hydroxylamines, nitriles, and related functional groups into alkynes, leading to valuable acrylamides. Various transition metals, including copper, nickel, iron, zinc, and palladium, play key roles in facilitating hydroamination, hydroboration, carbonylation, and other transformations. This review explores both recent metal-catalyzed and metal-free methodologies published in the last 15 years, emphasizing the importance of precise control over selectivity and functional-group compatibility.
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Related Concept Videos
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.
02:37Structure and Physical Properties of Alkynes
In nature, compounds containing both carbon and hydrogen are known as "hydrocarbons". Aliphatic hydrocarbons are compounds whose molecules contain saturated single bonds (i.e., alkanes) or unsaturated double or triple bonds. Alkenes contain carbon–carbon double bonds and have a structural formula CnH2n. Unsaturated hydrocarbons containing carbon–carbon triple bonds are called "alkynes" and are structurally represented by the formula CnH2n-2.
The...
02:34Preparation of Alkynes: Dehydrohalogenation
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
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.
02:42Acidity of 1-Alkynes
The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
02:39Nomenclature of Alkynes