Related Experiment Video
Updated: Aug 26, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Desulfinative Alkylation of Heteroarenes via an Electrostatic Electron Donor-Acceptor Complex
Ramkrishna Laha1, Twinkle I Patel1, Matthew J Moschitto1
1Department of Medicinal Chemistry Ernest Mario School of Pharmacy, Rutgers, the State University of New Jersey 163 Frelinghuysen Road, Piscataway New Jersey 08901, United States.
Abstract:
Functionalized pyridine and quinoline rings are important components of numerous bioactive molecules and natural products; however, diversification of these rings often requires de novo heterocycle ring synthesis or demanding reaction conditions. We report a method for desulfinative alkylation of pyridine and quinoline N-methoxide salts that operates under both photocatalytic and electrostatic electron donor-acceptor-mediated pathways. Unlike most EDA-mediated processes, this reaction operates in the absence of light and with the desulfination of the donor compound.
Related Concept Videos
α-Alkylation of Ketones via Enolate Ions
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...
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Acid Halides to Esters: Alcoholysis
Preparation of Alkynes: Dehydrohalogenation
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.

