Bachmann J (2006)
Publication Status: Published
Publication Type: Journal article, Original article
Publication year: 2006
Publisher: American Chemical Society
Book Volume: 71
Pages Range: 8706-8714
DOI: 10.1021/jo0613075
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.
APA:
Bachmann, J. (2006). Hangman salen platforms containing two xanthene scaffolds. Journal of Organic Chemistry, 71, 8706-8714. https://doi.org/10.1021/jo0613075
MLA:
Bachmann, Julien. "Hangman salen platforms containing two xanthene scaffolds." Journal of Organic Chemistry 71 (2006): 8706-8714.
BibTeX: Download