Abigail Doyle

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Abigail G. Doyle
Born1980 (age 40–41)
CitizenshipAmerican
Alma materHarvard University (A.B. (2002), A.M. (2002), Ph.D. (2008))
Stanford University
AwardsArthur C. Cope Scholar Award
Scientific career
FieldsOrganic Chemistry, Organometallic chemistry, Catalysis
InstitutionsUniversity of California, Los Angeles
Princeton University
ThesisEngaging alkyl halides and oxocarbenium ions in asymmetric catalysis (2008)
Doctoral advisorEric N. Jacobsen
Other academic advisorsJustin DuBois
Websitedoyle.princeton.edu

Abigail Gutmann Doyle is a Professor of Chemistry at the University of California, Los Angeles, where she holds the Saul Winstein Chair in Organic Chemistry.[1] From 2017 to July 2021, she was the A. Barton Hepburn Professor of Chemistry at Princeton University, where she had served on the faculty since 2008.[2] Her research focuses on the development of new chemical transformations in organic chemistry.

Early life and education[edit]

Doyle was born in NJ, Princeton in 1980 to Michael W. Doyle and Amy Gutmann, the eighth president of the University of Pennsylvania.[3]

Undergraduate years

Doyle studied both chemistry and chemical biology as an undergraduate at Harvard University, graduating with A.B. and A.M. degrees summa cum laude in 2002. During her undergraduate studies, she worked as an undergraduate research assistant at Harvard University in the lab of Prof. Eric N. Jacobsen. Doyle worked with then-postdoctoral fellow M. Christina White to study the mechanism of a novel iron-catalyzed epoxidation reaction of terminal alkenes and designing chiral ligands for an asymmetric variant of the reaction.[4]

While completing her undergraduate degree, Doyle was also a Pfizer Summer Undergraduate Research Fellow in 2001. In summer 2000, Doyle worked as an intern at Bristol Meyers Squibb. There, she studied the process aiding the preparation of the diabetes medication dapagliflozin.[5]

Graduate years

Doyle began her graduate career in 2002 as a DoD NDSEG Fellow in the laboratory of Justin DuBois at Stanford University, working on the preparation of Au(III) complexes and their reactivity for the hydration of unactivated alkenes.

In September 2003, Doyle transferred to Harvard University to continue her graduate work. Doyle performed her Ph.D. work under Prof. Eric N. Jacobsen, where she developed enantioselective alkylations with tributyltin enolates catalyzed by a Cr(salen)Cl catalyst.[6][7] She also worked alongside then-postdoctoral fellow Sarah Reisman to develop an approach for the enantioselective addition of nucleophiles to oxocarbenium ions, promoted by a novel thiourea organocatalyst.[8] Doyle also co-authored a Chemical Review article on hydrogen-bond donor catalysis.[9] During her graduate years, she received the Harvard College Certificate of Distinction in Teaching, the Sigma-Aldrich Graduate Student Innovation Award, and the Christensen Prize for Outstanding Research Achievement.

Career[edit]

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.[2]

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.[10]

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[11]
Figure 2: C-F Bond Formation by Pd (0)-Catalyzed Fluorination[12]

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.[13]

Figure 3: Ni-Catalyzed reaction of C(sp3)-H Cross-Coupling with Acyl Electrophiles[14]

Awards and honors[edit]

Some key awards of Doyle's independent career include the Alfred P. Sloan Foundation Fellowship (Alfred P. Sloan Foundation, 2012),[15] Amgen Young Investigator Award (2012), Arthur C. Cope Scholar Award (American Chemical Society, 2014),[16] 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).[17]

She is currently Senior Editor, Accounts of Chemical Research.[18]

Personal life[edit]

Doyle was married to economist Jakub W. Jurek in 2005 by a Baptist minister.[19] They met at Harvard.

References[edit]

  1. ^ Jennings, Penny (Jun 30, 2021). "Welcome Professor Abigail Doyle | UCLA Chemistry and Biochemistry". www.chemistry.ucla.edu. Retrieved 2021-07-01.
  2. ^ a b The Doyle Group Archived 2017-11-14 at the Wayback Machine, Princeton University
  3. ^ Abigail Doyle and Jakub Jurek, New York Times
  4. ^ White, M. Christina; Doyle, Abigail G.; Jacobsen, Eric N. (2001-07-01). "A Synthetically Useful, Self-Assembling MMO Mimic System for Catalytic Alkene Epoxidation with Aqueous H2O2". Journal of the American Chemical Society. 123 (29): 7194–7195. doi:10.1021/ja015884g. ISSN 0002-7863.
  5. ^ "C-Arylglucoside synthesis: triisopropylsilane as a selective reagent for the reduction of an anomeric C-phenyl ketal". Tetrahedron: Asymmetry. 14 (20): 3243–3247. 2003-10-17. doi:10.1016/j.tetasy.2003.08.007. ISSN 0957-4166.
  6. ^ Doyle, Abigail G.; Jacobsen, Eric N. (2005-01-01). "Enantioselective Alkylations of Tributyltin Enolates Catalyzed by Cr(salen)Cl:  Access to Enantiomerically Enriched All-Carbon Quaternary Centers". Journal of the American Chemical Society. 127 (1): 62–63. doi:10.1021/ja043601p. ISSN 0002-7863.
  7. ^ Doyle, Abigail G.; Jacobsen, Eric N. (2007). "Enantioselective Alkylation of Acyclic α,α-Disubstituted Tributyltin Enolates Catalyzed by a Cr(salen) Complex". Angewandte Chemie International Edition. 46 (20): 3701–3705. doi:10.1002/anie.200604901. ISSN 1521-3773.
  8. ^ Reisman, Sarah E.; Doyle, Abigail G.; Jacobsen, Eric N. (2008-06-01). "Enantioselective Thiourea-Catalyzed Additions to Oxocarbenium Ions". Journal of the American Chemical Society. 130 (23): 7198–7199. doi:10.1021/ja801514m. ISSN 0002-7863. PMC 2574628. PMID 18479086.
  9. ^ Doyle, Abigail G.; Jacobsen, Eric N. (2007-12-01). "Small-Molecule H-Bond Donors in Asymmetric Catalysis". Chemical Reviews. 107 (12): 5713–5743. doi:10.1021/cr068373r. ISSN 0009-2665.
  10. ^ 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.
  11. ^ 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
  12. ^ Katcher, M. H.; Norrby, P.-O.; Doyle, A. G. Mechanistic Investigations of Palladium-Catalyzed Allylic Fluorination. Organometallics. 2014, 33, 2121–2133
  13. ^ 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.
  14. ^ 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
  15. ^ "Past Fellows". sloan.org. Retrieved 2018-09-02.
  16. ^ Ritter, Stephen K. "2014 Arthur C. Cope Scholar Awards: Abigail G. Doyle | Chemical & Engineering News". cen.acs.org. Retrieved 2018-09-02.
  17. ^ "Abigail Doyle | Princeton University Department of Chemistry". chemistry.princeton.edu. Retrieved 2020-10-27.
  18. ^ "Editors". pubs.acs.org. Retrieved 2018-09-02.
  19. ^ "Abigail Doyle and Jakub Jurek". The New York Times. 2005-06-26. ISSN 0362-4331. Retrieved 2021-06-01.