Abigail G. Doyle | |
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Born | Princeton, New Jersey, U.S. | April 30, 1980
Alma mater | Harvard University (BA, MA, PhD) |
Parents |
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Awards | Arthur C. Cope Scholar Award, Elias J. Corey Award |
Scientific career | |
Fields | Organic Chemistry, Organometallic chemistry, Catalysis |
Institutions | University of California, Los Angeles Princeton University |
Thesis | Engaging alkyl halides and oxocarbenium ions in asymmetric catalysis (2008) |
Doctoral advisor | Eric N. Jacobsen |
Other academic advisors | Justin DuBois |
Notable students | Julia Kalow |
Website | doyle |
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] Her research focuses on the development of new chemical transformations in organic chemistry.
Doyle was born in Princeton, NJ in 1980 to Michael W. Doyle and Amy Gutmann, the eighth president of the University of Pennsylvania and current United States Ambassador to Germany. Doyle studied chemistry as an undergraduate at Harvard University, graduating with A.B. and A.M. degrees summa cum laude in 2002. In 2003, she went to Harvard University and joined the lab of Professor Eric Jacobsen. [2]
After beginning graduate studies in the lab of Justin DuBois at Stanford University, Doyle completed her Ph.D. under Prof. Eric N. Jacobsen, where she developed enantioselective alkylations with tributyltin enolates catalyzed by a Cr(salen)Cl catalyst. [3] [4] She also worked on the development of an enantioselective addition of nucleophiles to oxocarbenium ions. [5]
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. [6] In 2021, she moved to the University of California, Los Angeles, where she holds the Saul Winstein Chair in Organic Chemistry. [1]
Research
A longstanding research interest of the Doyle group is the development of nickel-catalyzed C–C bond forming reactions that utilize unconventional cross-coupling electrophiles, such as epoxides, aziridines, imminium ions, and oxocarbenium ions. The group has developed and mechanistically interrogated new ligands and pre-catalysts for nickel, which have helped to enable these transformations. In collaboration with David MacMillan's group, the Doyle lab identified a new cross-coupling paradigm which allows the combination of photoredox and nickel catalysis. [7] The Doyle lab has subsequently applied Nickel/photoredox catalysis to methodologies involving both unconventional and traditional cross-coupling electrophiles.
The group has also 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. These methods have employed both transition metal and photoredox catalysis, and the group has developed new reagents for mild and selective deoxyfluorination reactions.
Recently, the Doyle group has worked in the area of data science-driven analysis of chemical reactions, including the implementation of machine learning algorithms to model and predict reaction outcome in organic chemistry. [8] [9] [10]
Some key awards of Doyle's independent career include the Alfred P. Sloan Foundation Fellowship (Alfred P. Sloan Foundation, 2012), [11] Amgen Young Investigator Award (2012), Arthur C. Cope Scholar Award (American Chemical Society, 2014), [12] 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). [13]
She is currently Senior Editor, Accounts of Chemical Research . [14]
An enamine is an unsaturated compound derived by the condensation of an aldehyde or ketone with a secondary amine. Enamines are versatile intermediates.
In organic chemistry, a coupling reaction is a type of reaction in which two reactant molecules are bonded together. Such reactions often require the aid of a metal catalyst. In one important reaction type, a main group organometallic compound of the type R-M reacts with an organic halide of the type R'-X with formation of a new carbon-carbon bond in the product R-R'. The most common type of coupling reaction is the cross coupling reaction.
A pinacol coupling reaction is an organic reaction in which a carbon–carbon bond is formed between the carbonyl groups of an aldehyde or a ketone in presence of an electron donor in a free radical process. The reaction product is a vicinal diol. The reaction is named after pinacol, which is the product of this reaction when done with acetone as reagent. The reaction is usually a homocoupling but intramolecular cross-coupling reactions are also possible. Pinacol was discovered by Wilhelm Rudolph Fittig in 1859.
In organic chemistry, organocatalysis is a form of catalysis in which the rate of a chemical reaction is increased by an organic catalyst. This "organocatalyst" consists of carbon, hydrogen, sulfur and other nonmetal elements found in organic compounds. Because of their similarity in composition and description, they are often mistaken as a misnomer for enzymes due to their comparable effects on reaction rates and forms of catalysis involved.
Sir David William Cross MacMillan is a Scottish chemist and the James S. McDonnell Distinguished University Professor of Chemistry at Princeton University, where he was also the chair of the Department of Chemistry from 2010 to 2015. He shared the 2021 Nobel Prize in Chemistry with Benjamin List "for the development of asymmetric organocatalysis". MacMillan used his share of the $1.14 million prize to establish the May and Billy MacMillan Foundation.
Maurice S. Brookhart is an American chemist, and professor of chemistry at the University of Houston since 2015.
Hydrogen auto-transfer, also known as borrowing hydrogen, is the activation of a chemical reaction by temporary transfer of two hydrogen atoms from the reactant to a catalyst and return of those hydrogen atoms back to a reaction intermediate to form the final product. Two major classes of borrowing hydrogen reactions exist: (a) those that result in hydroxyl substitution, and (b) those that result in carbonyl addition. In the former case, alcohol dehydrogenation generates a transient carbonyl compound that is subject to condensation followed by the return of hydrogen. In the latter case, alcohol dehydrogenation is followed by reductive generation of a nucleophile, which triggers carbonyl addition. As borrowing hydrogen processes avoid manipulations otherwise required for discrete alcohol oxidation and the use of stoichiometric organometallic reagents, they typically display high levels of atom-economy and, hence, are viewed as examples of Green chemistry.
A metal salen complex is a coordination compound between a metal cation and a ligand derived from N,N′-bis(salicylidene)ethylenediamine, commonly called salen. The classical example is salcomine, the complex with divalent cobalt Co2+, usually denoted as Co(salen). These complexes are widely investigated as catalysts and enzyme mimics.
A Josiphos ligand is a type of chiral diphosphine which has been modified to be substrate-specific; they are widely used for enantioselective synthesis. They are widely used in asymmetric catalysis.
In organic chemistry, Lewis acid catalysis is the use of metal-based Lewis acids as catalysts for organic reactions. The acids act as an electron pair acceptor to increase the reactivity of a substrate. Common Lewis acid catalysts are based on main group metals such as aluminum, boron, silicon, and tin, as well as many early and late d-block metals. The metal atom forms an adduct with a lone-pair bearing electronegative atom in the substrate, such as oxygen, nitrogen, sulfur, and halogens. The complexation has partial charge-transfer character and makes the lone-pair donor effectively more electronegative, activating the substrate toward nucleophilic attack, heterolytic bond cleavage, or cycloaddition with 1,3-dienes and 1,3-dipoles.
Hydrogen-bond catalysis is a type of organocatalysis that relies on use of hydrogen bonding interactions to accelerate and control organic reactions. In biological systems, hydrogen bonding plays a key role in many enzymatic reactions, both in orienting the substrate molecules and lowering barriers to reaction. The field is relatively undeveloped compared to research in Lewis acid catalysis.
Asymmetric ion-pairing catalysis in chemistry is a type of asymmetric catalysis taking place specifically with charged intermediates or charged reagents. In one type of catalysis ion-pairing exists with a charged and chiral catalyst. The charged catalyst can be cationic or anionic. Catalysis by anionic catalysts is also called asymmetric counteranion-directed catalysis. In the other variation of asymmetric ion-pairing catalysis called anion or cation binding, the chiral catalyst is neutral but binds in a noncovalent way to an intermediate ion pair. Asymmetric ion-pairing catalysis is distinct from other covalent types of catalysis such as Lewis acid catalysis and Bronsted acid catalysis. It is one of several strategies in enantioselective synthesis and of some relevance to academic research.
Synergistic catalysis is a specialized approach to catalysis whereby at least two different catalysts act on two different substrates simultaneously to allow reaction between the two activated materials. While a catalyst works to lower the energy of reaction overall, a reaction using synergistic catalysts work together to increase the energy level of HOMO of one of the molecules and lower the LUMO of another. While this concept has come to be important in developing synthetic pathways, this strategy is commonly found in biological systems as well.
Photoredox catalysis is a branch of photochemistry that uses single-electron transfer. Photoredox catalysts are generally drawn from three classes of materials: transition-metal complexes, organic dyes, and semiconductors. While organic photoredox catalysts were dominant throughout the 1990s and early 2000s, soluble transition-metal complexes are more commonly used today.
Sarah Elizabeth Reisman is the Bren Professor of Chemistry and the Chair of Division of Chemistry and Chemical Engineering at California Institute of Technology. She received the (2013) Arthur C. Cope Scholar Award and the (2014) Tetrahedron Young Investigator Award for Organic Synthesis. Her research focuses on the total synthesis of complex natural products and data-driven developments of asymmetric catalysis.
Heterobimetallic catalysis is an approach to catalysis that employs two different metals to promote a chemical reaction. Included in this definition are cases where: 1) each metal activates a different substrate, 2) both metals interact with the same substrate, and 3) only one metal directly interacts with the substrate(s), while the second metal interacts with the first.
Cross electrophile coupling is a type of cross-coupling reaction that occurs between two electrophiles. It is often catalyzed by transition metal catalyst(s). Unlike conventional cross-coupling reactions of an electrophile with an organometallic reagent, the coupling partners in cross electrophile coupling reactions are both electrophiles. Generally, additional reductant to regenerate active catalyst is needed in this reaction.
Francisco Dean Toste is the Gerald E. K. Branch Distinguished Professor of Chemistry at the University of California, Berkeley and faculty scientist at the chemical sciences division of Lawrence Berkeley National Lab. He is a prominent figure in the field of organic chemistry and is best known for his contributions to gold chemistry and asymmetric ion-pairing catalysis. Toste was elected a member of the National Academy of Sciences in 2020, and a member of the American Academy of Arts and Sciences in 2018.
Thomas Lectka is an American organic chemist, academic and researcher. He is Jean and Norman Scowe Professor of Chemistry and leads the Lectka Group at Johns Hopkins University.
Louis Fensterbank is a French scientist specialized in molecular chemistry. Professor at Sorbonne University and Senior Member of Institut Universitaire de France, he has been the director of the Institut Parisien de Chimie Moléculaire since 2017.