Abigail Doyle

Abigail Gutmann Doyle is the A. Barton Hepburn Professor of Chemistry at Princeton University.[1] Her research focuses on the development of new chemical transformations.

Abigail Doyle
Born
Princeton, NJ
CitizenshipAmerican
EducationHarvard University
AwardsArthur C. Cope Scholar Award
Scientific career
FieldsChemistry
InstitutionsPrinceton University
Academic advisorsEric Jacobsen

Early life and education

Abigail Doyle was born in NJ, Princeton in 1980 to Michael W. Doyle and Amy Gutmann, the eighth president of the University of Pennsylvania.[2]

Undergraduate years

As an undergraduate, Doyle studied both chemistry and chemical biology at Harvard University and graduated with A.B. and A.M. degrees summa cum laude in 2002. During her undergraduate studies, she was a Pfizer Summer Undergraduate Research Fellow at the American Chemistry Society (ACS). From May to August 2000, Doyle worked as an intern at Bristol Meyers Squibb. There, she studied the process aiding the preparation of dapagliflozin. She also worked as an undergraduate research assistant at Harvard University in the lab of Eric Jacobsen. She worked with postdoctoral fellow M. Christina White studying the mechanism of a novel iron-catalyzed epoxidation reaction of terminal alkenes and designing chiral ligands for an asymmetric variant of the reaction.

Graduate years

Doyle began her graduate career as a National Defense Science and Engineering fellow at the DuBois Laboratory at Stanford University, working on the preparation of Au (III) complexes and their reactivity for the hydration of unactivated alkenes. In September 2003, she transferred to Harvard University to continue her graduate work. She performed her Ph.D. work in the Jacobsen laboratory and worked alongside Sarah Reisman. There she discovered an approach for the enantioselective addition of nucleophiles to oxocarbenium ions promoted by a thiourea catalyst. Doyle also co-authored a Chemical Review article on hydrogen-bond donor catalysis, which has received more than 1200 citations so far. Throughout her graduate years, she received the Harvard College Certificate of Distinction in Teaching as well as the Sigma-Aldrich Graduate Student Innovation Award and Christensen Prize for Outstanding Research Achievement.

Career
Independent career

In July 2008, Doyle was appointed as an Assistant Professor of Chemistry at Princeton University. She was promoted to the rank of Associate Professor with tenure in 2013, and to full Professor with an endowed chair, the A. Barton Hepburn Professor of Chemistry, in 2017.[1]

Research

During her independent career at Princeton, her group identified catalytic cross-coupling reactions with styrenyl epoxides and aziridines as electrophiles and pioneered several other important transformations using Ni-based catalysts. Her recent collaborative work with David MacMillan identified a new cross-coupling paradigm which allows the combination of photoredox and nickel catalysis.[3]

The group has been involved in the development of nucleophilic fluorination chemistry allowing the creation of pharmaceutically-relevant molecules with sp3-C-F and sp2-C-F bonds.

Figure 1: Copper-Catalyzed H-F Insertion Reaction Optimization[4]
Figure 2: C-F Bond Formation by Pd (0)-Catalyzed Fluorination[5]

Another ongoing project the group is working on is Ni-catalyzed cross coupling. They aim to develop new cross-coupling reactions with classic aliphatic electrophiles, which includes epoxides, aziridines, or acetals. As shown by the figure below, metallaphotoredox catalysis assisted by nickel mediates the C(sp3)-H acylation. The group has developed an air-stable Nickel precatalyst that works in a variety of known Nickel-catalyzed transformations.[6]

Figure 3: Ni-Catalyzed reaction of C(sp3)-H Cross-Coupling with Acyl Electrophiles[7]

Awards and honors

Some key awards of Doyle's independent career include the Alfred P. Sloan Foundation Fellowship (Alfred P. Sloan Foundation, 2012),[8] Amgen Young Investigator Award (2012), Arthur C. Cope Scholar Award (American Chemical Society, 2014),[9] Bayer Early Excellence in Science Award (2013), Phi Lambda Upsilon National Fresenius Award (Phi Lamba Upsilon, 2014), Presidential Early Career Award for Scientists and Engineers (PECASE, 2014) BMS Unrestricted Grant in Synthetic Organic Chemistry (2016).

She is currently Senior Editor, Accounts of Chemical Research.[10]

References
  1. The Doyle Group, Princeton University
  2. Abigail Doyle and Jakub Jurek, New York Times
  3. Zuo, Zhiwei; Ahneman, Derek T.; Chu, Lingling; Terrett, Jack A.; Doyle, Abigail G.; MacMillan, David W. C. (2014-07-25). "Merging photoredox with nickel catalysis: Coupling of α-carboxyl sp3-carbons with aryl halides". Science. 345 (6195): 437–440. doi:10.1126/science.1255525. ISSN 0036-8075. PMC 4296524. PMID 24903563.
  4. Gray, E. E.; Nielsen, M. K.; Choquette, K. A.; Kalow, J. A.; Graham, T. J. A.; Doyle, A. G. Nucleophilic (Radio)Fluorination of α-Diazocarbonyl Compounds Enabled by Copper-Catalyzed H–F Insertion J. Am. Chem. Soc. 2016, 138, 10802−10805
  5. Katcher, M. H.; Norrby, P.-O.; Doyle, A. G. Mechanistic Investigations of Palladium-Catalyzed Allylic Fluorination. Organometallics. 2014, 33, 2121–2133
  6. Shields, Jason D.; Gray, Erin E.; Doyle, Abigail G. (2015-04-17). "A Modular, Air-Stable Nickel Precatalyst". Organic Letters. 17 (9): 2166–2169. doi:10.1021/acs.orglett.5b00766. ISSN 1523-7060. PMC 4719147. PMID 25886092.
  7. Joe, C. L.; Doyle, A. G. Direct Acylation of C(sp3)−H Bonds Enabled by Nickel and Photoredox Catalysis Angew. Chem. Int. Ed. 2016, 55, 4040-4043
  8. "Past Fellows". sloan.org. Retrieved 2018-09-02.
  9. Ritter, Stephen K. "2014 Arthur C. Cope Scholar Awards: Abigail G. Doyle | Chemical & Engineering News". cen.acs.org. Retrieved 2018-09-02.
  10. "Editors". pubs.acs.org. Retrieved 2018-09-02.
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