Related Experiment Video
Updated: May 6, 2026

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
Borata-alkene derivatives conveniently made by frustrated Lewis pair chemistry
Juri Möbus1, Gerald Kehr, Constantin G Daniliuc
1Organisch-Chemisches Institut, Universität Münster, Corrensstraße 40, 48149 Münster, Germany. erker@uni-muenster.de.
Abstract:
Two (aryl)PXY starting materials (aryl = mesityl or 2,4,6-triisopropylphenyl; X,Y = Cl, Br) were reacted with lithiated conjugated enynes (derived from 2-methylbutenyne or 1-ethynylcyclohexene) to yield the respective (aryl)bis(enynyl)phosphanes. Their reaction with HB(C6F5)2 gave the heterocyclic five-membered zwitterionic borata-diene compounds containing the aryl group and one unchanged enynyl substituent at phosphorus. The borata-alkene products were thought to arise from a two step process of regioselective alkyne hydroboration followed by an internal phosphane attack on the boryldiene unit. Three examples of the ring-closed borata-alkene type products were characterized by X-ray diffraction.
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.
Preparation 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.
Introduction to Electrophilic Addition Reactions of Alkenes
Addition and elimination...
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.
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Hydroboration-Oxidation of Alkenes

