Benzylic C(sp3)-C(sp2) cross-coupling of indoles enabled by oxidative radical generation and nickel catalysis
Weonjeong Kim1, Jangwoo Koo1, Hong Geun Lee1
1Department of Chemistry, College of Natural Science, Seoul National University 1 Gwanak-ro Seoul 08826 South Korea hgleee@snu.ac.kr.
Abstract:
A mechanistically unique functionalization strategy for a benzylic C(sp3)-H bond has been developed based on the facile oxidation event of indole substrates. This novel pathway was initiated by efficient radical generation at the benzylic position of the substrate, with subsequent transition metal catalysis to complete the overall transformation. Ultimately, an aryl or an acyl group could be effectively delivered from an aryl (pseudo)halide or an acid anhydride coupling partner, respectively. The developed method utilizes mild conditions and exhibits a wide substrate scope for both substituted indoles and C(sp2)-based reaction counterparts. Mechanistic studies have shown that competitive hydrogen atom transfer (HAT) processes, which are frequently encountered in conventional methods, are not involved in the product formation process of the developed strategy.
More Related Videos
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
Published on: June 20, 2014
11:44Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
Published on: March 20, 2014
Related Concept Videos
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism
Reactions at the Benzylic Position: Oxidation and Reduction
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
Nucleophilic Aromatic Substitution: Elimination–Addition
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Electrophilic Aromatic Substitution: Nitration of Benzene
