4.4 Article

Transition-metal free highly selective aerobic oxidation of hindered 2-alkylindoles

Journal

TETRAHEDRON
Volume 71, Issue 34, Pages 5531-5537

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2015.06.065

Keywords

Condensation; Indole; Aerobic oxidation; Basic media and aprotic solvent

Funding

  1. Alzahra University
  2. Iran National Science Foundation (INSF)

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A novel and easy access to highly complex 3-oxoindolin-2-ylidene derivatives from the exposure of Ugiadducts bearing an indolyl moiety in Cs2CO3/DMF to air is reported. This is the first example of aerobic oxidation of 2-alkylindoles to 3-oxoindolin-2-ylidenes. Some advantages of this method are the use of air as oxygen source, transition metal-free reagents and simple conditions, a multicomponent and one-pot process and highly regio- and stereoselective manner to trans-3-oxoindolin-2-ylidenes. (C) 2015 Elsevier Ltd. All rights reserved.

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