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‘High-Surface Sodium' as a Reducing Agent for TiCl3

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Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Seidel,  Günter
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Fürstner, A., & Seidel, G. (1995). ‘High-Surface Sodium' as a Reducing Agent for TiCl3. Synthesis, (1), 63-68. doi:10.1055/s-1995-3854.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0014-A487-8
Abstract
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.