Related Experiment Video
Updated: Jun 28, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Rhodium(III)-Catalyzed Switchable β-C(sp2)-H Alkenylation and Alkylation of Acyclic Enamides with Allyl Alcohols
Xiaolan Li1,2, Jie Liu2, Ruixin Song2
1College of Chemistry, Nanchang University, Nanchang, Jiangxi 330031, China.
Abstract:
Herein, rhodium(III)-catalyzed β-C(sp2)-H alkenylation and alkylation of enamides are presented using readily accessible allylic alcohols by switching the reaction conditions. This tunable transformation has been applied to a wide range of substrates and typically proceeded with excellent regioselectivity and stereoselectivity as well as with good functional group tolerance. The catalytic system offers an efficient approach for synthesizing various functionalized enamides bearing N-(2Z,4E)-butadiene and (Z)-β-C(sp2)-H alkylated enamides. In addition, mechanistic experiments suggest that Rh(III)-catalyzed C-H activation is not related to the critical step.
Related Concept Videos
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
Radical Anti-Markovnikov Addition to Alkenes: Overview
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
α-Alkylation of Ketones via Enolate Ions
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.

