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Reductively Stable Hydrogen-Bonding Ligands Featuring Appended CF2-H Units
James P Shanahan1, Danielle M Mullis1, Matthias Zeller2
1Department of Chemistry, University of Michigan, 930 N. University, Ann Arbor, Michigan 48109, United States.
Abstract:
We present the development of ligands featuring the unconventional hydrogen bond donor, -CF2H, within a metal's secondary coordination sphere. When metalated with palladium, o-CF2H-functionalized 1,10-phenanthroline provides highly directed H-bonding interactions with Pd-coordinated substrates. Spectroscopic and computational analyses with a series of X-type ligand acceptors (-F, -Cl, -Br, -OR) establish the H-bonding interaction strength for the -CF2H group (∼3 kcal/mol). The synthesis of Pd0/Ni0 complexes and subsequent coupling (Ni) highlight the unique reductive and base compatibility of the -CF2H hydrogen bond donor group.
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