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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Nickel-Catalyzed Boron-Mediated Saturative Trifunctionalization of Alkynes
Shanglin Chen1, Yaru Peng1, Junmei Lin1
1Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry, State Key Laboratory of Green and Efficient Development of Phosphorus Resources, Fuzhou University, Fuzhou, China.
Abstract:
Converting simple alkynes into fully substituted alkanes-installing three distinct groups via a sequential one‑pot process-remains a formidable challenge. Herein, we report a boron-mediated, nickel-catalyzed strategy that achieves this transformation, enabling the modular assembly of valuable 1,1-diarylalkanes from both simple alkynyl tetracoordinate borons and N-acylglutarimides. The reaction proceeds with high regio- and chemoselectivity under mild conditions, exhibiting good functional group tolerance across both coupling partners. Mechanistic studies support a unique reaction pathway involving dual 1,2-metallate shifts, with water serving as the terminal proton source. The synthetic utility is demonstrated through one-pot synthesis, late-stage functionalization of drugs, gram-scale reactions, and versatile downstream transformations of the products. This strategy represents a distinct strategy that differs from stepwise alkyne reduction, offering a useful disconnection for complex alkane synthesis starting from alkynyl tetracoordinate borons or terminal alkynes via one‑pot borylation.
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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.
03:08Hydroboration-Oxidation of Alkenes
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.
02:38Electrophilic 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.
02:36Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
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.