Forming Phenanthrenes by Using MoCl5

Forming Phenanthrenes by Using MoCl5

Author: Hayley Charville

The synthesis of phenanthrene derivatives is of increasing interest owing to the diverse biological and pharmacological properties of these compounds, including antitumor and antibacterial activities. Although there are several routes to phenanthrene derivatives, many of these methods suffer from poor atom economy and a large number of linear steps.

Siegfried R. Waldvogel, Mainz University, Germany, and co-workers have developed a C–C coupling reaction of 2-aryl-substituted cinnamates (1) to form the corresponding phenanthrene derivatives (2), in yields up to 99 %, by using a MoCl5/TiCl4 reagent mixture.
Forming Phenanthrenes by Using MoCl5

This oxidation reaction is easy to perform, and the best results are obtained when the 2-phenyl substituent of the cinnamate is equipped with two methoxy groups. Importantly, the high rate of C–C bond formation can tolerate a variety of substituents that are not compatible with other reagents.

This simple, inexpensive, but powerful method emphasizes the effectiveness of MoCl5 or MoCl5/TiCl4 in oxidative coupling reactions.

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