Jennifer Roizen

Overview:

Inspired by small molecule natural products, the Roizen laboratories will initiate research to access improved antibiotics, and selective ion channel inhibitors, with implications for the study and treatment of cancer, heart disease, and neurological disorders. This program will begin with the development of novel reaction methods, and where appropriate these methodologies will be advanced through mechanistic investigations. New reactions will be designed to streamline access to challenging natural products, such as the guaianolide sesquiterpenes. Access to these small molecules will enable us to collaborate with colleagues to probe the biological activity of these molecular architectures.

Positions:

Assistant Professor of Chemistry

Chemistry
Trinity College of Arts & Sciences

Member of the Duke Cancer Institute

Duke Cancer Institute
School of Medicine

Education:

B.A. 2003

Williams College

Ph.D. 2009

California Institute of Technology

Postdoctoral Fellow, Chemistry

Stanford University

Grants:

MRI: Acquisition of a Triple Quadrupole LC/MS System

Administered By
Chemistry
Awarded By
National Science Foundation
Role
Major User
Start Date
End Date

Acquisition of a MALDI-TOF Mass Spectrometer System at Duke University

Administered By
Chemistry
Awarded By
North Carolina Biotechnology Center
Role
Major User
Start Date
End Date

GAANN - Department of Chemistry

Administered By
Chemistry
Awarded By
Department of Education
Role
Mentor
Start Date
End Date

Exploiting Masked Alcohols to Guide Atom-Transfer Reactions

Administered By
Chemistry
Role
Principal Investigator
Start Date
End Date

Exploring the Limits of Electroorganic Synthesis Productivity with Flow-Through Nanowire Electrodes

Administered By
Chemistry
Awarded By
American Chemical Society
Role
Co-Principal Investigator
Start Date
End Date

Publications:

Alcohol and amine derivatives guide position-selective C-H functionalization reactions

Authors
MLA Citation
Roizen, Jennifer. “Alcohol and amine derivatives guide position-selective C-H functionalization reactions.” Abstracts of Papers of the American Chemical Society, vol. 258, 2019.
URI
https://scholars.duke.edu/individual/pub1467686
Source
wos-lite
Published In
Abstracts of Papers of the American Chemical Society
Volume
258
Published Date

Sulfamate esters guide selective alkylation at traditionally non-reactive gamma-C(sp3)-H bonds

Authors
Kanegusuku, AG; Castanheiro, T; Roizen, J
MLA Citation
Kanegusuku, Anastasia Gant, et al. “Sulfamate esters guide selective alkylation at traditionally non-reactive gamma-C(sp3)-H bonds.” Abstracts of Papers of the American Chemical Society, vol. 256, AMER CHEMICAL SOC, 2018.
URI
https://scholars.duke.edu/individual/pub1440471
Source
wos
Published In
Abstracts of Papers of the American Chemical Society
Volume
256
Published Date

Photochemically Mediated Nickel-Catalyzed Synthesis of <i>N</i>-(Hetero)aryl Sulfamides.

A general method for the <i>N</i>-arylation of sulfamides with aryl bromides is described. The protocol leverages a dual-catalytic system, with [Ir(ppy)<sub>2</sub>(dtbbpy)]PF<sub>6</sub> as a photosensitizer, NiBr<sub>2</sub>·glyme as a precatalyst, and 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU) as a base, and proceeds at room temperature under visible light irradiation. Using these tactics, aryl boronic esters and aryl chlorides can be carried through the reaction untouched. The developed reactions efficiently engage simple bromoarenes and primary sulfamides in between 66% and quantitative yields. For more challenging substrates, such as secondary sulfamides, the reaction efficiency is documented. Thereby, these methods complement the known Buchwald-Hartwig coupling methods for <i>N</i>-arylation of sulfamides.
Authors
Simons, RT; Scott, GE; Kanegusuku, AG; Roizen, JL
MLA Citation
Simons, R. Thomas, et al. “Photochemically Mediated Nickel-Catalyzed Synthesis of N-(Hetero)aryl Sulfamides.The Journal of Organic Chemistry, vol. 85, no. 10, May 2020, pp. 6380–91. Epmc, doi:10.1021/acs.joc.0c00139.
URI
https://scholars.duke.edu/individual/pub1438525
PMID
32312047
Source
epmc
Published In
The Journal of Organic Chemistry
Volume
85
Published Date
Start Page
6380
End Page
6391
DOI
10.1021/acs.joc.0c00139

Modifying Positional Selectivity in C-H Functionalization Reactions with Nitrogen-Centered Radicals: Generalizable Approaches to 1,6-Hydrogen-Atom Transfer Processes

Authors
Short, MA; Blackburn, JM; Roizen, JL
MLA Citation
Short, Melanie A., et al. “Modifying Positional Selectivity in C-H Functionalization Reactions with Nitrogen-Centered Radicals: Generalizable Approaches to 1,6-Hydrogen-Atom Transfer Processes.” Synlett, vol. 31, no. 2, GEORG THIEME VERLAG KG, Jan. 2020, pp. 102–16. Wos, doi:10.1055/s-0039-1691501;ArtID:st-2019-p0583-sp.
URI
https://scholars.duke.edu/individual/pub1428958
Source
wos
Published In
Synlett
Volume
31
Published Date
Start Page
102
End Page
116
DOI
10.1055/s-0039-1691501;ArtID:st-2019-p0583-sp

Sulfamides direct radical-mediated chlorination of aliphatic C-H bonds

Given the prevalence of aliphatic amines in bioactive small molecules, amine derivatives are opportune as directing groups. Herein, sulfamides serve as amine surrogates to guide intermolecular chlorine-transfer at γ-C(sp ) centers. This unusual position-selectivity arises because accessed sulfamidyl radical intermediates engage preferentially in otherwise rare 1,6-hydrogen-atom transfer (HAT) processes through seven-membered transition states. The site-selectivity of C-H abstraction can be modulated by adjusting the steric and electronic properties of the sulfamide nitrogen substituents, an ability that has not been demonstrated with other substrate classes. The disclosed reaction relies on a light-initiated radical chain-propagation mechanism to oxidize C(sp )-H bonds efficiently. 3 3
Authors
Short, MA; Shehata, MF; Sanders, MA; Roizen, JL
MLA Citation
Short, M. A., et al. “Sulfamides direct radical-mediated chlorination of aliphatic C-H bonds.” Chemical Science, vol. 11, no. 1, Jan. 2020, pp. 217–23. Scopus, doi:10.1039/c9sc03428e.
URI
https://scholars.duke.edu/individual/pub1427426
Source
scopus
Published In
Chem. Sci.
Volume
11
Published Date
Start Page
217
End Page
223
DOI
10.1039/c9sc03428e

Research Areas:

Chemistry
Chemistry (general)
Chemistry Techniques, Synthetic
Chemistry, Organic
Heterocyclic Compounds
Pharmaceutical chemistry
Protective groups (Chemistry)
Radicals (Chemistry)
Reaction mechanisms (Chemistry)