Related Experiment Video
Updated: Jun 5, 2025

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Gearing Effects on N-9-Anth-PyBidine-Cu(OAc)2-Catalyzed Asymmetric Direct Haloimidation Reactions of
Yuri Takagi1, Takaaki Saito1, Natsuki Mizuno1
1Soft Molecular Activation Research Center (SMARC), Chiba Iodine Resource Innovation Center (CIRIC), Synthetic Organic Chemistry, Department of Chemistry, Graduate School of Science, Chiba University, 1-33 Yayoi, Inage, Chiba 263-8522, Japan.
Abstract:
A newly developed N-9-anthranylmethyl bis(imidazolidine)pyridine (N-9-Anth-PyBidine)-Cu(OAc)2 complex catalyzed asymmetric haloimidation reactions of alkylidenemalononitriles with N-bromosuccinimide and N-chlorosuccinimide, employing the succinimide moiety directly as a copper-bound nucleophile. The anthranyl substituent showed a gearing effect that produced a well-organized asymmetric sphere involving the N-H proton of the imidazolidine ring in the ligand. The gearing effect afforded hydrogen bonding-assisted copper-catalyzed haloimidation reactions with high enantioselectivity.
More Related Videos
06:46Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
19:58Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
Related Concept Videos
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...
Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution
Base-Promoted α-Halogenation of Aldehydes and Ketones
α-Alkylation of Ketones via Enolate Ions
Nucleophilic Aromatic Substitution: Elimination–Addition
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3