Related Experiment Video
Updated: Mar 18, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Solvated electron-driven hydroamination of olefins
Anietie W Williams1, Kerry M Gilmore1,2
1Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269, USA. kerry.m.gilmore@uconn.edu.
None:
We report a transition metal-free method for the intermolecular hydroamination of olefins using solvated electrons, generated in situ from granulated lithium under sonication in 2-methyltetrahydrofuran (2-MeTHF). This additive-free protocol enables rapid formation of mixed secondary and tertiary amines under ambient conditions and is broadly applicable to vinylarenes and alkyl amines. Selected allylarenes and conjugated dienes are also competent substrates, exhibiting distinct regioselectivity under the reaction conditions. Mechanistic studies support an SET and HAT pathway, with lithium amide intermediates acting as both reductants and nucleophiles. The method offers excellent atom economy, sustainability, and synthetic utility, exemplified by the selective synthesis of the pharmaceutical benzphetamine in high yield.
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
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis
During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...
Hydroboration-Oxidation of Alkenes
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.
Acid-Catalyzed Dehydration of Alcohols to Alkenes
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...