Access to 3-Oxindoles from Allylic Alcohols and Indoles

Hortense Lauwick (1) , Yang Sun (1) , Huriye Akdas-Kilig (1) , Sylvie Dérien (1) , Mathieu Achard (1)

1 ISCR - Institut des Sciences Chimiques de Rennes

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.

Keywords: allylation; fluorescence; metathesis; oxidation; ruthenium

Domains: Chemical Sciences

Hortense Lauwick, Yang Sun, Huriye Akdas-Kilig, Sylvie Dérien, Mathieu Achard. Access to 3-Oxindoles from Allylic Alcohols and Indoles. Chemistry - A European Journal, 2018, 24 (31), pp.7964-7969. ⟨10.1002/chem.201800348⟩. ⟨hal-01834006⟩