Robert Grossman
University of Kentucky, KY·Chemistry
Many useful molecules contain two nitrogen-bearing amine groups sitting on neighboring carbon atoms, an arrangement called a 1,2-diamine. These patterns are common in natural products, serve as the backbone of catalysts that speed up chemical reactions, and appear in materials used in advanced manufacturing.
- Fields
Chemistry
- Topics
1,2-diamines
azimines
1,3-dipolar cycloaddition
- Grants
- 1 known grant, through Jul 2029
What they work on
- Define the scope of 1,2-diamination by testing 1,3-dipolar cycloadditions of azimines, a barely studied class of three-nitrogen dipoles, with both electron-poor and electron-neutral alkenes to form substituted 1,2,3-triazolidines.
- Convert the resulting 1,2,3-triazolidine rings into 1,2-diamines by hydrogenation, confirming that the nitrogen protecting groups installed by the azimine can be removed cleanly.
- Establish whether the cycloaddition is reliably stereospecific, so that the geometry of the starting alkene determines the relative arrangement of the two amine groups in the product.
- Develop intramolecular variants in which the azimine and alkene are tethered in a single molecule, as a route to ring-containing 1,2-diamines.
- Develop asymmetric variants of the azimine cycloaddition that favor one mirror-image form of the 1,2-diamine product.
More about the research
The obstacle is practical: making 1,2-diamines from cheap, ordinary starting materials is still difficult, which limits how widely industry can use them. This project sets out to build them from alkenes, hydrocarbons with a carbon-carbon double bond that are among the most abundant and inexpensive feedstocks in organic chemistry, in a way that is faster, safer and less costly than current routes.
Why it matters
Compounds with two neighboring amine groups are building blocks for reaction catalysts and manufacturing materials, but current syntheses are costly and hard to run at scale. A route that converts cheap alkenes into these diamines in few steps, with control over three-dimensional shape, could make them more accessible to chemical and pharmaceutical manufacturers. The project also brings high school students into a working chemistry laboratory through ChemCamp.
Known grants
From NIH and NSF research grants. Labs often have other funding we can't see.
Closest labs
Ramesh Giri
Pennsylvania State University, PA·Chemistry
Develop transition-metal-catalyzed difunctionalization of alkenes bearing simple functional groups, using a dual ligand system of electron-deficient alkenes and organic nitriles to stabilize intermediates and promote C(sp3)–C(sp3) bond formation.
Aaron Aponick
University of Georgia, GA·Chemistry
Identify Pd(II)-StackPhos catalysts, palladium paired with a chiral imidazole-based biaryl ligand, that give high mirror-image selectivity in alkene 1,2-difunctionalization for both syn- and anti-addition.
Mark Biscoe
CUNY City College, NY·Chemistry
Develop palladium- and copper-catalyzed cross-coupling reactions that transfer handedness from enantioenriched secondary alkylboron reagents to new carbon centers with predictable retention or inversion.
The school
University of Kentucky: 34 labs on PI Pages, $528M a year on research, 319 research doctorates a year.
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