Related Experiment Video
Updated: Apr 17, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Aza-Wacker-type reaction between electron-deficient olefins and N-alkylsulfonamides
Huayou Hu1, Jiaxin Tian, Yun Liu
1Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University , Huaian 223300, P. R. China.
Abstract:
A palladium-catalyzed oxidative amination protocol of electron-deficient olefins by aza-Wacker-type reaction with N-alkylsulfonamides was developed. The presence of the stoichiometric amount of methanesulfonic acid was crucial for the success of this transformation. The reactions were conducted in green solvent under mild conditions and scalable with excellent E-type stereoselectivity. In addition, a Pd(II)/Pd(0) catalytic cycle with the existence of a very strong oxidant (Selectfluor) was proposed.
More Related Videos
08:12A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
05:34Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
Related Concept Videos
Preparation and Reactions of Sulfides
Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character, phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom...
Oxidative Cleavage of Alkenes: Ozonolysis
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
Acid Halides to Esters: Alcoholysis
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.
Amines to Alkenes: Hofmann Elimination
Under thermal conditions, the hydroxide can abstract a proton from the β carbon; this generates an alkene with the simultaneous...