Access to 3-Oxindoles from Allylic Alcohols and Indoles

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Lauwick H., Sun Y., Akdas-Kilig H., Derien S., Achard M.

CHEMISTRY-A EUROPEAN JOURNAL, vol.24, no.31, pp.7964-7969, 2018 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 24 Issue: 31
  • Publication Date: 2018
  • Doi Number: 10.1002/chem.201800348
  • Journal Name: CHEMISTRY-A EUROPEAN JOURNAL
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.7964-7969
  • Keywords: allylation, fluorescence, metathesis, oxidation, ruthenium, CYCLOPENTADIENYL RUTHENIUM COMPLEX, RING-CLOSING METATHESIS, ENANTIOSELECTIVE ALLYLATION, DEAROMATIZATION REACTION, OXIDATIVE REARRANGEMENT, CYCLOADDITION REACTIONS, DEHYDRATIVE ALLYLATION, 2-SUBSTITUTED INDOLES, CATALYZED ALLYLATION, ASYMMETRIC CATALYSIS
  • Yıldız Technical University Affiliated: No

Abstract

The site-selective and regioselective allylation of 2-substituted indoles was performed by using a ruthenium(IV) precatalyst containing a phosphine-sulfonate chelate. Mono-, di-, and triallylated indoles were selectively obtained depending on the reaction conditions with the formation of water as the only byproduct. The preparation of 3-oxindole derivatives was then successfully performed owing to air oxidation of the corresponding allylated indoles. Diallylated pseudoindoxyls were proven to be good synthons to perform cyclization through a ring-closing metathesis reaction to afford the corresponding tricyclic adducts. The photophysical properties of the 3-oxindoles were measured, and some of the compounds showed strong fluorescence in water.