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Synthesis 1995; 1995(1): 63-68
DOI: 10.1055/s-1995-3854
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‘High-Surface Sodium’ as a Reducing Agent for TiCl3

Alois Fürstner* , Günter Seidel
  • *Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, D-45470 Mülheim/Ruhr, Germany
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Publication Date:
31 December 2000 (online)

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Sodium deposited on inorganic supports such as Al2O3, TiO2 and NaCl (‘high-surface sodium’) is a cheap, readily prepared, nonpyrophoric reducing agent for TiCl3. The low-valent titanium thus obtained, after only 1 h reduction time, is well suited for McMurry coupling reactions, particularly of aromatic carbonyl compounds. It exhibits a previously unrivalled template effect for the cyclization of dicarbonyl compounds to (macrocyclic) cycloalkenes and is suitable for the reduction of N-acyl-2-aminobenzophenone derivatives to 2,3-disubstituted indoles. Even a 36-membered ring could be formed without recourse to high dilution techniques.

metal activation - McMurry reaction - macrocyclization - template effect - supported reagents - sodium