Nickel-catalyzed remote hydrosilylation of unconjugated enones with bulky triphenylsilane
Related Experiment Video
Updated: Oct 21, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Xue Chen1, Zhen Wang1, Jinyong Zhou1
1College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, 310014, China. zhoubw@zjut.edu.cn.
Abstract:
Herein we describe a nickel-catalyzed remote hydrosilylation of unconjugated enones with bulky triphenylsilane. A range of Z-silyl enol ethers are obtained as major isomers due to the process of nickel triggered alkene isomerization. Notably, some specific alkyl silyl enol ethers can be prepared from this protocol, which are not easily accessed by the traditional strategy using a strong base and chlorosilane. This reaction features 100% atom economy, simple reaction conditions, and good yields.
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.
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
α-Alkylation of Ketones via Enolate Ions
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...
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Dehydration of Aldols to Enones: Acid-Catalyzed Aldol Condensation

