Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 71, Issue 23, Pages 8706-8714Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo0613075
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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 salicyladehyde, 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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