PIPages
Labs

Ramesh Giri

Pennsylvania State University, PA·Chemistry

Many medicines are built around a core of carbon atoms joined in specific patterns, and making those cores efficiently is a central challenge in chemistry. One powerful shortcut is to add two carbon pieces across a carbon-carbon double bond, found in molecules called alkenes, forming two new carbon-carbon bonds in a single step.

Fields

Chemistry

Topics

alkene difunctionalization

dicarbofunctionalization

unactivated alkenes

Grants
1 known grant, through May 2029

What they work on

  1. 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.
  2. Develop photoredox catalysis using light-excited dioxygen and catalytic iodine to add two carbon groups across alkenes lacking coordinating groups, including forming strained cyclopropane rings.
  3. Create enantioselective versions of these alkene dicarbofunctionalization reactions, which yield a single mirror-image product, by designing TADDOL-phosphoramidite, PyOx and BOX chiral ligands.

More about the research

This is hard for simple "unactivated" alkenes. They react sluggishly, and the reactive intermediate formed after the first carbon is added tends to fall apart before the second can be attached.

Why it matters

Faster, shorter routes to complex carbon frameworks could make it cheaper and simpler to build molecular motifs found in pharmaceuticals, bioactive molecules and drug targets. Chemists in drug discovery and synthesis could use these one-step, two-bond-forming reactions to construct molecules that other methods cannot easily reach.

Known grants

From NIH and NSF research grants. Labs often have other funding we can't see.

New Directions in Alkene Difunctionalization Reactions

NIH · Sep 2019 – May 2029

Closest labs

Xiaodong Shi

University of Maryland, MD·Chemistry

Optimize triazole-ruthenium carbene (TA-Ru) catalysts, whose triazole ligands improve heat stability, for olefin metathesis reactions that previous catalysts handled poorly, including high-temperature transformations.

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.

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.

The school

Pennsylvania State University: 60 labs on PI Pages, $1.3B a year on research, 743 research doctorates a year.

More about Pennsylvania State University

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