Related Experiment Video
Updated: Jun 6, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Ruthenium(ii) catalyzed C-3 site selective alkenylation of indole derivatives via C-H activation
Jithender Rallabandi1,2, Smrutiranjan Mohanty2, Indrajit Shown1
1Department of Chemistry, Hindustan Institute of Technology and Science Chennai 603103 India indrajits@hindustanuniv.ac.in shownindrajit@gmail.com.
Abstract:
An efficient synthetic method has been developed for C-3 site-selective alkenylation of indole derivatives under ruthenium(ii) catalysis with an ester as a directing group. Besides the presence of two potential C(sp2)-H sites available for functionalization in the substrates, exclusive C3 selectivity was achieved in a selective manner as only mono-functionalized products were formed. The high site selectivity is attributed to the formation of an uncommon six-membered metallacycle intermediate between the ruthenium catalyst and ester directing group, enabled by the selective alkenylation at the C3 position of indole derivatives. This protocol features high site selectivity, operational simplicity, broad substrate scope, and moderate to high yields.
More Related Videos
07:30A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
Published on: January 21, 2020
10:51The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
Published on: April 10, 2015
Related Concept Videos
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
α-Alkylation of Ketones via Enolate Ions
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.