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Mechanistic studies on the CAN-mediated intramolecular cyclization of ?-aryl-?-dicarbonyl compounds.

ABSTRACT: The synthesis of 2-tetralones through the cyclization of ?-aryl-?-dicarbonyl substrates by using CAN is described. Appropriately functionalized aromatic substrates undergo intramolecular cyclizations generating 2-tetralone derivatives in moderate to good yields. DFT computational studies indicate that successful formation of 2-tetralones from ?-aryl-?-dicarbonyl radicals is dependent on the stability of the subsequent cyclohexadienyl radical intermediates. Furthermore, DFT computational studies were used to rationalize the observed site selectivity in the 2-tetralone products.

SUBMITTER: Casey BM

PROVIDER: S-EPMC3740710 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature

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Mechanistic studies on the CAN-mediated intramolecular cyclization of δ-aryl-β-dicarbonyl compounds.

Casey Brian M BM Sadasivam Dhandapani V DV Flowers Ii Robert A RA

Beilstein journal of organic chemistry 20130723

The synthesis of 2-tetralones through the cyclization of δ-aryl-β-dicarbonyl substrates by using CAN is described. Appropriately functionalized aromatic substrates undergo intramolecular cyclizations generating 2-tetralone derivatives in moderate to good yields. DFT computational studies indicate that successful formation of 2-tetralones from δ-aryl-β-dicarbonyl radicals is dependent on the stability of the subsequent cyclohexadienyl radical intermediates. Furthermore, DFT computational studies ...[more]

PMID: 23946845

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