Abigail Doyle Group – Professor Product Portal

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Professor 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.

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Wu K1, Doyle AG1.
2017 Aug;9(8):779-784. doi: 10.1038/nchem.2741. Epub 2017 Mar 6.
The field of Ni-catalysed cross-coupling has seen rapid recent growth because of the low cost of Ni, its earth abundance, and its ability to promote unique cross-coupling reactions. Whereas advances in the related field of Pd-catalysed cross-coupling have been driven by ligand design, the development of ligands specifically for Read More
Ariki ZT1, Maekawa Y1, Nambo M2, Crudden CM1,2
2018 Jan 10;140(1):78-81. doi: 10.1021/jacs.7b10855. Epub 2017 Dec 21.
We describe the development of a nickel-catalyzed Suzuki-Miyaura cross-coupling of tertiary benzylic and allylic sulfones with arylboroxines. A variety of tertiary sulfones, which can easily be prepared via a deprotonation-alkylation route, were reacted to afford symmetric and unsymmetric quaternary products in good yields. We hRead More
Chung-Yang Dennis Huang, Abigail G Doyle
Journal of the American Chemical Society 2015-05-06
A Ni-catalyzed Negishi cross-coupling with 1,1-disubstituted styrenyl aziridines has been developed. This method delivers valuable β-substituted phenethylamines via a challenging reductive elimination that affords a quaternary carbon. A novel electron-deficient olefin ligand, Fro-DO, proved crucial for achieving high rates and c...Read More
Jason D Shields, Erin E Gray, Abigail G Doyle
Organic Letters 2015-05-01
The synthesis and catalytic activity of [(TMEDA)Ni(o-tolyl)Cl], an air-stable, crystalline solid, is described. This complex is an effective precatalyst in a variety of nickel-catalyzed transformations. The lability of TMEDA allows a wide variety of ligands to be used, including mono- and bidentate phosphines, diimines, and N-he...Read More
Zhiwei Zuo, Derek T Ahneman, Lingling Chu, Jack A Terrett, Abigail G Doyle, David W C MacMillan
Science 2014-07-25
Over the past 40 years, transition metal catalysis has enabled bond formation between aryl and olefinic (sp(2)) carbons in a selective and predictable manner with high functional group tolerance. Couplings involving alkyl (sp(3)) carbons have proven more challenging. Here, we demonstrate that the synergistic combination of photo...Read More
Daniel K Nielsen, Chung-Yang Dennis Huang, Abigail G Doyle
Journal of the American Chemical Society 2013-09-11
Herein we report a nickel-catalyzed C-C bond-forming reaction between simple alkyl aziridines and organozinc reagents. This method represents the first catalytic cross-coupling reaction employing a nonallylic and nonbenzylic Csp(3)-N bond as an electrophile. Key to its success is the use of a new N-protecting group (cinsyl or Cn...Read More
Jason D Shields, Derek T Ahneman, Thomas J A Graham, Abigail G Doyle
Organic Letters 2014-01-03
Quinolinium ions are engaged in an asymmetric, Ni-catalyzed Suzuki cross-coupling to yield 2-aryl- and 2-heteroaryl-1,2-dihydroquinolines. Key to the development of this method is the use of a Ni(II) precatalyst that activates without the need for strong reductants or high temperatures. The Ni-iminium activation mode is demonstr...Read More
Chung-Yang Huang, Abigail G Doyle
Journal of the American Chemical Society 2012-06-13
A nickel-catalyzed cross-coupling reaction between N-sulfonyl aziridines and organozinc reagents is reported. The catalytic system comprises an inexpensive and air-stable Ni(II) source and dimethyl fumarate as ligand. Regioselective synthesis of β-substituted amines is possible under mild and functional-group-tolerant conditions...Read More
Thomas J A Graham, R Frederick Lambert, Karl Ploessl, Hank F Kung, Abigail G Doyle
Journal of the American Chemical Society 2014-04-09
Herein, we describe an operationally straightforward radiosynthesis of a chiral transition metal fluoride catalyst, [(18)F](salen)CoF, and its use for late-stage enantioselective aliphatic radiofluorination. We demonstrate the utility of the method by preparing single enantiomer experimental and clinically validated PET tracers ...Read More