Related Experiment Video
Updated: Dec 7, 2025

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Silver(I) Oxide-/DBU-Promoted Synthesis of Dihydrofuran Units through Allenyl Silver Formation
Bao Yu1, Anna Perfetto2, Luca Allievi1
1Faculté des Sciences Pharmaceutiques et Biologiques, Unité CNRS UMR 8038 CiTCoM, Université de Paris Descartes, 4 avenue de l'Observatoire, 75270, Paris Cedex 06, France.
Abstract:
A formal [3+2] cyclization mediated by silver(I) oxide and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) is described herein. Through a broad variety of carbonyl compounds, this system can promote cyclization reactions with high yield (up to 85 %) and diastereoselectivity (up to 95:5) for a straightforward access to complex and congested dihydrofuran derivatives in one step under mild conditions. Based on DFT studies, the proposed mechanism would involve an allenyl silver intermediate.
Related Concept Videos
Preparation and Reactions of Sulfides
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Formation of Complex Ions
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.

