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Ruthenium(II)-catalyzed synthesis of pyrrole- and indole-fused isocoumarins by C-H bond activation in DMF and water

DRS at CSIR-National Institute of Oceanography

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Title Ruthenium(II)-catalyzed synthesis of pyrrole- and indole-fused isocoumarins by C-H bond activation in DMF and water
 
Creator Singh, K.S.
Sawant, S.G.
Dixneuf, P.H.
 
Subject AQUATIC RESOURCES
CHEMISTRY AND BIOGEOCHEMISTRY
CHEMISTRY AND BIOGEOCHEMISTRY
 
Description Pyrrole- and indole-fused isocoumarins constitute important structural units in natural products and pharmacophores, although the direct and selective bifunctionalization of pyrrole and indole remain a challenge. Herein, we report a one-pot synthesis of pyrrole- and indole-fused isocoumarins from simple 1-methylpyrrole-2-carboxylic acid and 1-methylindole-3-carboxylic acid by annulation with alkynes in the presence of a ruthenium(II) catalyst based on [RuCl2(p-cymene)]2 with Cu(OAc)2-H2O as the oxidant in DMF. This ruthenium(II)-catalyzed transformation was shown to be profitably performed in water as the solvent. The reaction, which involves carboxylate coordination, activation of the heterocyclic sp2 C-H bond, and insertion of the alkyne, is regioselective, which leads to good yields of the isocoumarins
 
Date 2016-05-12T12:00:17Z
2016-05-12T12:00:17Z
2016
 
Type Journal Article
 
Identifier ChemCatChem Communication, vol.8(6); 2016; 1046-1050
no
http://drs.nio.org/drs/handle/2264/4962
 
Language en
 
Relation ChemCatChem_8_1046.jpg
 
Rights Prior to publication, the Contributor must include the following notice on the preprint: “This is a preprint of an article accepted for publication in ChemCatChem Communication. Copyright © [2016] WILEY-VCH Verlag GmbH & Co. ”. After publication of the Contribution by Wiley, the preprint notice should be amended to read as follows: “This is a preprint of an article published in [ChemCatChem Communication, vol.8(6); 2016; 1046-1050]”and an electronic link to the Journal’s WWW site, located at the following Wiley URL: http://onlinelibrary.wiley.com/doi/10.1002/cctc.201501261/abstract. The Contributor agrees not to update the preprint or replace it with the published version of the Contribution.
 
Publisher Wiley