- CHE 230: Mechanistic Organic Chemistry I
- CHE 231: Mechanistic Organic Chemistry I Laboratory
- CHE 237: Mechanistic Organic Chemistry I Laboratory
- CHE 239: Mechanistic Organic Chemistry II Laboratory
- CHE 378: Applied Spectroscopy
Vadola's research focuses on the development
of new methods for the synthesis of organic molecules with a particular
emphasis C–H bond functionalization. C–H bonds are ubiquitous in
organic molecules but classically have been viewed as fairly unreactive,
thus causing them to be overlooked as potential functional handles in
organic synthesis. The field of C–H bond functionalization is focused on
exploring new methods to directly convert these unreactive bonds into
more desirable functionalities, such as C–C, C–N, and C–O bonds, through
the formation of reactive intermediates (Figure 1, intermediates
highlighted in blue). By this approach, valuable organic molecules with
significant structural complexity may be accessed in a concise manner
from simple C–H-bond-containing precursors. This ability to selectively
functionalize a targeted C–H bond can provide new routes to chemical
structures previously inaccessible by classical organic chemistry.
His group's approach to reaction design is target driven with the goal
of developing new methods that grant access to chemical structures found
in pharmaceuticals and naturally occurring medicinally active
molecules. They are particularly interested in new approaches to the
synthesis of spirocycles. Spirocyclic scaffolds of varying complexity
are prevalent in a variety of organic molecules, ranging from
biologically active natural products and pharmaceuticals to organic
materials (Figure 2). The fully substituted carbon center that defines
this broad class of compounds makes them a particularly attractive
target to synthetic organic chemists. The group is currently
investigating new catalytic methods of generating complex spirocyclic
structures within the setting of natural product synthesis.
In addition to the development of new chemical reactions, he
is interested in using synthetic organic chemistry as a means to develop
chemical tools for the study of biological systems. The balance of
various chemical processes within the cell is responsible for
maintaining proper cellular function, and disruption of this balance can
lead to a disease state. One area of research in his group will focus
on developing fluorescent molecules that will enable in vivo imaging of the cellular environment as a means to study the physiochemical changes that occur in diseased tissue.
- Paul A. Vadola and
Dalibor Sames “Intramolecular Coupling of sp2 C–H Bonds and Alkynes for
the Synthesis of Coumarins: Exploring the Scope and Application to the
Development of Neuroimaging Agents.” J. Org. Chem., 2012,77, 7804-7814.
- Paul A. Vadola,
Ignacio Carrera, and Dalibor Sames “C–H Bond Functionalization via
Hydride Transfer: Formation of a-Arylated Piperidines and
1,2,3,4-Tetrahydroisoquinolines via Stereoselective Intramolecular
Amination of Benzylic C-H Bonds.” J. Org. Chem., 2012, 77, 6689-6702. Published as a Featured Article and Featured on the Cover of volume 77, issue 18.
- Rebecca M. Wilson, Jennifer L. Stockdill, Xiangyang Wu, Xuechen Li, Paul A. Vadola,
Peter K. Park, Ping Wang, and Samuel J. Danishefsky “A Fascinating
Journey into History: Exploration of the World of Isonitriles En Route
to Complex Amides.” Angew. Chem. Int. Ed., 2012, 51, 2834-2848.
- Paul A. Vadola and
Dalibor Sames “C–H Bond Functionalization via Hydride Transfer: Direct
Coupling of Unactivated Alkynes and sp3 C–H Bonds Catalyzed by Platinum
Tetraiodide” J. Am. Chem. Soc., 2009, 131, 16525-16528.
- Niko G. Gubernator, Hui Zhang, Ronald G. W. Staal, Eugene V. Mosharov, Daniela Pereira, Minerva Yue, Vojtech Balsanek, Paul A. Vadola,
Bipasha Mukherjee, Robert H. Edwards, David Sulzer, and Dalibor Sames
“Fluorescent False Neurotransmitters Visualize Dopamine Release from
Individual Presynaptic Terminals” Science, 2009, 324, 1441-1444.
Professional Society Memberships
- American Chemical Society