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Articles by Thomas Lectka
Close Amide NH···F Hydrogen Bonding Interactions in 1,8-Disubstituted Naphthalenes
The interaction of C–F bonds, especially in proteins, with proximate functional groups is a topic of lively interest and discussion.(1−6) Their importance in dictating protein structure and function is not yet fully answered, including the dilemma of whether such interactions themselves are due to propinquity, attractive interactions, or a combination thereof.
Fluorofunctionalization of C═C Bonds with Selectfluor: Synthesis of β-Fluoropiperazines through a Substrate-Guided Reactivity Switch
The halofunctionalization of alkene substrates remains an essential tool for synthetic chemists. Herein, we report regioselective ammoniofluorination of unactivated alkenes through photochemical means. A one-pot transformation of the ammonium fluoride products into pharmaceutically relevant β-fluoropiperazines is highlighted.
Catalyzed and Promoted Aliphatic Fluorination
Desta Doro Bume , Stefan Andrew Harry, Thomas Lectka*, and Cody Ross Pitts*† Department of Chemistry, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218 , United States † Department of Chemistry and Applied Biosciences, ETH Zürich, Vladimir-Prelog-Weg 2, 8093 Zürich, Switzerland J. Org.
Spectroscopic Characterization of a [C-F-C]+ Fluoronium Ion in Solution
We report the first spectroscopic evidence for a [C-F-C]+ fluoronium ion in solution. Extensive NMR studies (19F, 1H, 13C) characterize a symmetrical cage-like species in which fluorine exhibits substantial covalent bonding to each of the two carbon atoms involved in the three-center interaction. Experimental NMR data comport well with calculated values to lend credence to the structural assignment.
Fluorine in a C-F Bond as the Key to Cage Formation
Cage molecules have long been employed to trap reactive or fleeting species, as their rigid nature allows them to enforce situations that otherwise would not persist. In this minireview, we discuss our use of rigid cage structures to investigate the close noncovalent interactions of fluorine with other functional groups and determine how mutual proximity affects both physical properties and reactivity.
Aminofluorination of Cyclopropanes: A Multifold Approach through a Common, Catalytically Generated Intermediate
We have discovered a highly regioselective aminofluorination of cyclopropanes. Remarkably, four unique sets of conditions—two photochemical, two purely chemical—generated the same aminofluorinated adducts in good to excellent yields. The multiple, diverse ways in which the reaction could be initiated provided valuable clues that led to the proposal of a “unifying” chain propagation mechanism beyond initiation, tied by a common intermediate.
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