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Cobalt-catalyzed highly diastereoselective [3 + 2] carboannulation reactions: facile access to substituted indane
Arnab Dey1, Anurag Singh1, Chandra M R Volla1
1Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai-400076, India. chandra.volla@chem.iitb.ac.in.
Abstract:
Efficient oxidative [3 + 2] annulation reaction involving aryl hydrazones and heterobicyclic alkenes has been realized with inexpensive and earth-abundant cobalt salts under aerobic conditions. The reaction proceeds via directing-group-assisted C-H activation and exo-selective migratory insertion, followed by the intramolecular nucleophilic attack of the alkylcobalt(III) species onto the imine with high anti-diastereoselectivity to provide complex indane derivatives. The generation of three contiguous stereogenic centers within the indanyl unit and the avoidance of the use of stoichiometric amounts of metal oxidants make this transformation more valuable and appealing.
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