Indole Synthesis through Sequential Electrophilic N-H and C-H Bond Activation Using Iodine(III) Reactivity
Laura Fra1, Kilian Muñiz2,3
1Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.
Abstract:
An intramolecular approach towards the regioselective construction of 2,3-diarylated indoles is reported. The reaction follows an intramolecular electrophilic N-H and C-H bond functionalization between the aniline and acetylene. This methodology employs the concept of a traceless tether to provide access to the free 2,3-diarylated indole products comprising a total of 18 examples. Hypervalent iodine reagents were identified as suitable promoters and four different protocols are provided, including stoichiometric and catalytic transformations.
More Related Videos
10:14Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
Published on: May 16, 2014
07:30A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
Published on: January 21, 2020
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Cycloaddition Reactions: Overview
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.
α-Alkylation of Ketones via Enolate Ions
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
