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Doyle Group – Professor Product Portal

Abigail Doyle

Professor Abigail Doyle


Research in the Doyle group focuses on two areas: nucleophilic fluorination and nickel catalysis. The Doyle group has developed several reagents that advance these research areas. In fluorination, 2-pyridinesulfonyl fluoride (PyFluor) can be used for the mild deoxyfluorination of primary and secondary alcohols, a procedure which is normally accomplished by the sensitive reagent DAST. In nickel catalysis, the Doyle group has developed a modular, air-stable nickel precatalyst, [(TMEDA)Ni(o-tolyl)Cl], which has broad utility for a wide variety of reactions. This precatalyst can be used in place of Ni(cod)2, NiCl2, as well as other reported precatalysts. Doyle has also reported electron-deficient olefin ligands as a new class of ligand for accelerated reductive elimination. In particular, the sultam-derived ligand Fro-DO has been found to be critical for high yields in the cross-coupling of tertiary aziridines to form quaternary centers.

Doyle Group Website

Recent papers from the Doyle Group

1.
Wu K, Doyle AG. 2017. Parameterization of phosphine ligands demonstrates enhancement of nickel catalysis via remote steric effects. Nature Chem. 9(8):779-784. https://doi.org/10.1038/nchem.2741
2.
Ariki ZT, Maekawa Y, Nambo M, Crudden CM. 2018. Preparation of Quaternary Centers via Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling of Tertiary Sulfones. J. Am. Chem. Soc.. 140(1):78-81. https://doi.org/10.1021/jacs.7b10855
3.
Huang C(, Doyle AG. 2015. Electron-Deficient Olefin Ligands Enable Generation of Quaternary Carbons by Ni-Catalyzed Cross-Coupling. J. Am. Chem. Soc.. 137(17):5638-5641. https://doi.org/10.1021/jacs.5b02503
4.
Shields JD, Gray EE, Doyle AG. 2015. A Modular, Air-Stable Nickel Precatalyst. Org. Lett.. 17(9):2166-2169. https://doi.org/10.1021/acs.orglett.5b00766
5.
Zuo Z, Ahneman DT, Chu L, Terrett JA, Doyle AG, MacMillan DWC. 2014. Merging photoredox with nickel catalysis: Coupling of  α-carboxyl sp3-carbons with aryl halides. Science. 345(6195):437-440. https://doi.org/10.1126/science.1255525
6.
Nielsen DK, Huang C(, Doyle AG. 2013. Directed Nickel-Catalyzed Negishi Cross Coupling of Alkyl Aziridines. J. Am. Chem. Soc.. 135(36):13605-13609. https://doi.org/10.1021/ja4076716
7.
Shields JD, Ahneman DT, Graham TJA, Doyle AG. 2014. Enantioselective, Nickel-Catalyzed Suzuki Cross-Coupling of Quinolinium Ions. Org. Lett.. 16(1):142-145. https://doi.org/10.1021/ol4031364
8.
Huang C(, Doyle AG. 2012. Nickel-Catalyzed Negishi Alkylations of Styrenyl Aziridines. J. Am. Chem. Soc.. 134(23):9541-9544. https://doi.org/10.1021/ja3013825
9.
Graham TJA, Lambert RF, Ploessl K, Kung HF, Doyle AG. 2014. Enantioselective Radiosynthesis of Positron Emission Tomography (PET) Tracers Containing [18F]Fluorohydrins. J. Am. Chem. Soc.. 136(14):5291-5294. https://doi.org/10.1021/ja5025645
Products available from the Doyle Group:
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DISCIPLINES

  • Organic Synthetic Chemistry
  • Catalysis

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