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Polycyclic Aromatic Hydrocarbons via Iron(III)-Catalyzed Carbonyl–Olefin Metathesis

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posted on 21.02.2017, 12:18 by Christopher C. McAtee, Paul S. Riehl, Corinna S. Schindler
Polycyclic aromatic hydrocarbons are important structural motifs in organic chemistry, pharmaceutical chemistry, and materials science. The development of a new synthetic strategy toward these compounds is described based on the design principle of iron­(III)-catalyzed carbonyl–olefin metathesis reactions. This approach is characterized by its operational simplicity, high functional group compatibility, and regioselectivity while relying on FeCl3 as an environmentally benign, earth-abundant metal catalyst. Experimental evidence for oxetanes as reactive intermediates in the catalytic carbonyl–olefin ring-closing metathesis has been obtained.