Mark Levin
University of Chicago, IL·Chemistry·Early-career
Chemists usually build molecules by stitching pieces together. A newer idea, molecular editing, instead changes a finished molecule one atom at a time — deleting a nitrogen, swapping a carbon for a nitrogen, replacing a sulfur — while leaving the rest of the structure untouched.
- Fields
Chemistry
- Topics
skeletal editing
molecular editing
nitrogen deletion
- Grants
- 3 known grants, through Jun 2031
What they work on
- Develop regioselective syntheses of pyrazoles, triazoles, imidazoles, and related azoles by sulfur-to-nitrogen skeletal editing, using thiadiazine-S-oxide and thiatriazine intermediates that form a carbon–nitrogen bond and then extrude sulfur monoxide.
- Establish selective N-alkylation and N-arylation of azoles using phase-transfer catalysis, Mitsunobu chemistry, nucleophilic aromatic substitution, and copper-catalyzed coupling, and extend the strategy to ring-fused azoles and peptide-relevant amino acid derivatives.
- Design improved anomeric amide reagents that avoid the decomposition routes of current reagents, using a computation-aided structure–activity survey, so weakly nucleophilic amines can undergo nitrogen deletion.
- Determine why different amine substrate classes partition isodiazene intermediates down different pathways, and use those rules to develop nitrogen insertion, pericyclic rearrangement, and deaminative functionalization reactions.
- Develop carbon-to-nitrogen atom replacement reactions that convert benzene rings into pyridines and higher-order nitrogen analogs, aiming at replacement of any carbon in any arene or heteroarene.
- Make atom-replacement reactions scalable and functional-group tolerant by substituting milder reagents for the highly oxidizing components of first-generation methods, and extend editing to sulfur- or oxygen-to-carbon replacement that installs exocyclic substituents.
More about the research
That ability matters because drug, agrochemical, and materials discovery often hinges on small changes to a ring system, and reaching those variants by conventional synthesis can mean starting over. These projects develop such single-atom editing reactions, work out how they operate mechanistically, and apply them to ring systems that medicinal chemists use constantly.
Why it matters
Azoles and pyridine-type rings are among the most common structural motifs in pharmaceuticals, agrochemicals, and functional materials. Methods that install a single nitrogen in a chosen position, or edit one atom of a finished molecule, could let discovery chemists test design ideas directly instead of resynthesizing compounds, and could cut the solvent, reagent, and separation waste associated with regioisomer mixtures — benefits for drug and crop-protection manufacturing as well as for fundamental synthetic chemistry.
Known grants
From NIH and NSF research grants. Labs often have other funding we can't see.
Closest labs
Gregory Fu
California Institute of Technology, CA·Chemistry
Develop nickel- and copper-catalyzed substitution reactions that couple families of alkyl electrophiles and nucleophiles not previously shown to react together, including highly hindered substrates.
Michael Young
University of Toledo, OH·Chemistry·Early-career
Develop regioselective arylation of free amine-tethered internal alkenes with aryl halides, using transient directing groups (temporary guiding groups for the catalyst) and changes in reaction conditions to control which carbon is functionalized.
Mary Watson
University of Delaware, DE·Chemistry
Develop enantioselective copper-catalyzed additions of alkynes to cyclic oxocarbenium and iminium ions, positively charged ring intermediates, to make oxygen and nitrogen heterocycles with tri- and tetrasubstituted stereocenters next to the heteroatom.
The school
University of Chicago: 39 labs on PI Pages, $681M a year on research, 457 research doctorates a year.
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