Related Experiment Video
Updated: Jan 8, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Visible-Light-Promoted Catalytic Redox-Neutral Alkynylation of Alkyl Boronic Acids/Boronates
Amit Behera1, Akash Bisoyi1, Veera Reddy Yatham1
1School of Chemistry, Indian Institute of Science Education and Research, Thiruvananthapuram 695551, India.
Abstract:
We present a catalytic, redox-neutral strategy for producing internal alkynes through the cross-coupling of alkyl boronic acids and boronates with (hetero)aryl acetylenic bromides. This method proceeds under mild conditions, requires no metal catalysts, and accommodates a wide variety of substrates including medicinally relevant molecules. Mechanistic investigations indicate the in situ formation of a boronate anion complex along with the generation of an alkyl radical under the reaction conditions.
More Related Videos
Related Concept Videos
Alkynes 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.
Hydroboration-Oxidation of Alkenes
Reduction 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.
Regioselectivity 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.
α-Alkylation of Ketones via Enolate Ions
Alcohols from Carbonyl Compounds: Reduction
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...

