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Access to 3‐Oxindoles from Allylic Alcohols and Indoles
Author(s) -
Lauwick Hortense,
Sun Yang,
AkdasKilig Huriye,
Dérien Sylvie,
Achard Mathieu
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201800348
Subject(s) - allylic rearrangement , computer science , chemistry , combinatorial chemistry , organic chemistry , catalysis
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.