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Doyle Group – Professor Product Portal

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

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

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

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

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

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

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

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

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

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:

DISCIPLINES

Organic Synthetic Chemistry
Catalysis

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