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Hangman salen platforms containing two xanthene scaffolds

Hangman salen platforms containing two xanthene scaffolds

Journal of Organic Chemistry 71(23): 8706-8714

A synthetic strategy for the construction of chiral salen ligands bearing two rigid xanthene spacers functionalized with carboxylic acid and ester groups is presented. Suzuki cross-coupling methodology is used to furnish the appropriately functionalized xanthene spacers to a salicylaldehyde, which is subsequently condensed with (1R,2R)-(-)-1,2-diaminocyclohexane to produce salen ligands featuring an expandable molecular cleft capable of multiple hydrogen-bonding interactions in addition to metallosalen oxidation chemistry. The ability of these "Hangman" platforms to support multielectron chemistry mediated by proton-coupled electron transfer (PCET) is established by their proclivity to promote the catalytic disproportionation of hydrogen peroxide to oxygen and water via a high-valent metal oxo. Within this functionalized Hangman framework, the stereochemistry of the cyclohexyl backbone of the salen platform is revealed in the epoxidation of 1,2-dihydronaphthalene by the metal oxo.

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Accession: 049187450

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PMID: 17080997

DOI: 10.1021/jo0613075

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