Reductively Stable Hydrogen-Bonding Ligands Featuring Appended CF2–H Units
- 30 April 2020
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 142 (19), 8809-8817
- https://doi.org/10.1021/jacs.0c01718
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.Funding Information
- University of Michigan
- Camille and Henry Dreyfus Foundation
- National Institute of General Medical Sciences (1R01GM111486-01A1)
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