Related Experiment Video
Updated: Jul 26, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Iridium-Catalyzed Enantioselective Formal α-Allylic Alkylation of Acrylonitrile
Pankaj Roy1, Santanu Mukherjee1
1Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.
Abstract:
A highly enantioselective formal α-allylic alkylation of acrylonitrile is developed using 4-cyano-3-oxotetrahydrothiophene (c-THT) as a safe and easy-to-handle surrogate of acrylonitrile. This two-step process consists of an Ir(I)/(P,olefin)-catalyzed branched-selective allylic alkylation using easily accessible branched rac-allylic alcohols as the allylic electrophile followed by retro-Dieckmann/retro-Michael fragmentation and is shown to be applicable for the enantioselective synthesis of α-allylic acrylates as well as α-allylic acrolein.
More Related Videos
09:54Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
Published on: September 12, 2018
09:58Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Related Concept Videos
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.
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.
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...
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.
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis