Palladium-Catalyzed Dearomative syn-1,4-Carboamination with Grignard Reagents
Conghui Tang1, Mikiko Okumura1, Yunbo Zhu1
1Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, IL, 61801, USA.
Abstract:
A protocol for palladium-catalyzed dearomative functionalization of simple, nonactivated arenes with Grignard reagents has been established. This one-pot method features a visible-light-mediated [4+2] cycloaddition between an arene and an arenophile, and subsequent palladium-catalyzed allylic substitution of the resulting cycloadduct with a Grignard reagent. A variety of arenes and Grignard reagents can participate in this process, forming carboaminated products with exclusive syn-1,4-selectivity. Moreover, the dearomatized products are amenable to further elaborations, providing functionalized alicyclic motifs and pharmacophores. For example, naphthalene was converted into sertraline, one of the most prescribed antidepressants, in only four operations. Finally, this process could also be conducted in an enantioselective fashion, as demonstrated with the desymmetrization of naphthalene.
More Related Videos
19:58Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
11:16Preparation of Silver-Palladium Alloyed Nanoparticles for Plasmonic Catalysis under Visible-Light Illumination
Published on: August 18, 2020
Related Concept Videos
Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents
Esters to Alcohols: Grignard Reaction
The reaction requires two equivalents of the Grignard reagent and introduces two identical alkyl groups, derived from the Grignard reagent, bonded to the hydroxyl-bearing carbon of the alcohol.
The reaction follows the typical nucleophilic acyl substitution mechanism. The Grignard...
Nitriles to Ketones: Grignard Reaction
The mechanism begins with a nucleophilic attack by the Grignard...
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism
Acid-Catalyzed Ring-Opening of Epoxides
Base-Catalyzed Ring-Opening of Epoxides
![Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F51444.jpg&w=3840&q=50)