Protocol for efficient dearomatization of N-heteroaromatics with halogen(I) complex catalyst
Shunya Oishi1, Takeshi Fujinami2, Yu Masui1
1Institute for Molecular Science, Okazaki, Aichi 444-8787, Japan; SOKENDAI (The Graduate University for Advanced Studies), Okazaki, Aichi 444-8787, Japan.
Abstract:
In this protocol, we describe the application of a halogen(I) complex as a highly active non-metallic complex catalyst. Specifically, we present a detailed guide to synthesize the halogen(I) complex catalyst and utilize it as an anion-binding catalyst for the Mukaiyama-Mannich-type reaction of N-heteroaromatics such as pyridines. By utilizing a simple catalyst preparation approach and relatively low catalyst loading, the steps outlined in this protocol contribute to the rapid development of useful substances such as pharmaceuticals and functional materials. For complete details on the use and execution of this protocol, please refer to Oishi et al. (2022).1.
More Related Videos
07:06A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
12:07Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Related Concept Videos
ortho–para-Directing Deactivators: Halogens
Base-Promoted α-Halogenation of Aldehydes and Ketones
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion 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...
α-Halogenation of Carboxylic Acid Derivatives: Overview
Radical Halogenation: Thermodynamics
