Synthesis of 3,3'-Disubstituted Indolenines Utilizing the Lewis Acid Catalyzed Alkylation of 2,3-Disubstituted Indoles with Trichloroacetimidates

Trichloroacetimidates function as effective electrophiles for the selective C3-alkylation of 2,3-disubstituted indoles to provide 3,3'-disubstituted indolenines. These indolenines are common synthetic intermediates that are often utilized in the synthesis of complex molecules. Effective reaction conditions utilizing Lewis acid catalysts have been determined, and the scope of the reaction with respect to indole and imidate reaction partner has been investigated. This chemistry provides an alternative to base promoted and transition metal catalyzed methods that are more commonly utilized to access similar indolenines.

Medienart:

E-Artikel

Erscheinungsjahr:

2017

Erschienen:

2017

Enthalten in:

Zur Gesamtaufnahme - volume:28

Enthalten in:

Synlett : accounts and rapid communications in synthetic organic chemistry - 28(2017), 17 vom: 12. Okt., Seite 2335-2339

Sprache:

Englisch

Beteiligte Personen:

Adhikari, Arijit A [VerfasserIn]
Radal, Léa [VerfasserIn]
Chisholm, John D [VerfasserIn]

Links:

Volltext

Themen:

Alkylation
Catalysis
Indole
Indolenine
Journal Article
Lewis Acid
Trichloroacetimidate

Anmerkungen:

Date Revised 01.10.2020

published: Print-Electronic

Citation Status PubMed-not-MEDLINE

doi:

10.1055/s-0036-1588491

funding:

Förderinstitution / Projekttitel:

PPN (Katalog-ID):

NLM277022738