Related Experiment Video
Updated: Sep 30, 2025

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
Published on: October 18, 2019
Hydroxyselenylation and Tethered Silanoxyselenylation of Allylic Silanols
Harshit Joshi1, Shyam Sathyamoorthi1
1Department of Medicinal Chemistry, University of Kansas, Lawrence, Kansas 66047, United States.
Abstract:
We present protocols for the highly regioselective hydroxyselenylation and silanoxyselenylation of allylic silanols. N-(Phenylseleno)phthalimide acts as the selenylating agent for both transformations. Under basic conditions, hydroxyselenylation proceeds with >20:1 regioselectivity, and the products are valuable synthons for further transformations. We show that the silanol plays a critical role in maintaining the yield and regioselectivity of this reaction. Surprisingly, under acidic conditions, the hydroxyselenylation pathway is blocked, and products of a tethered silanoxyselenylation are exclusive.
Related Concept Videos
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Preparation and Reactions of Sulfides
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
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.
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.
Alkynes 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.

