Elizabeth C. Swift

AbbVie (United States)

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Elizabeth R. Jarvo

University of California, Irvine

Bruce H. Lipshutz

University of California, Santa Barbara

T.A. Butler

University of California, Santa Barbara

Joshua D. Waetzig

University of Kansas

Shashank Shekhar

AbbVie (United States)

Brian Kotecki

AbbVie (United States)

Hanna M. Wisniewska

Pfizer (United States)

Corey R. J. Stephenson

University of Michigan–Ann Arbor

Theresa M. Williams

United States Military Academy

Buck L. H. Taylor

University of Portland

Cooperative Institutions

AbbVie (United States)

Pfizer (United States)

Abbott (United States)

Abbott Fund

Janssen (United States)

University of California, Irvine

University of Notre Dame

University of Michigan–Ann Arbor

University of Illinois Urbana-Champaign

University of Wisconsin–Madison

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ChemInform Abstract: Heterogeneous Catalysis with Nickel‐on‐Graphite (Ni/C_g)

ChemInform (2008)

T.A. Butler Elizabeth C. Swift Bruce H. Lipshutz

Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

10.1002/chin.200820247

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Citations (0)

A durable semiconductor photocatalyst

Science (2019)

Elizabeth C. Swift

Mesoporous graphitic carbon nitride robustly performs organic photoredox reactions

10.1126/science.aax8940

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Citations (33)

Direct Determination of Available Phosphoric Acid by Titration of Ammonium Phosphomolybdate

Journal of AOAC INTERNATIONAL (1952)

H R Allen Elizabeth C. Swift Ron D. Hays Z F Kaufman

Journal Article Direct Determination of Available Phosphoric Acid by Titration of Ammonium Phosphomolybdate Get access H R Allen, H R Allen Kentucky Agricultural Experiment Station, Lexington, Kentucky Search for other works by this author on: Oxford Academic Google Scholar Elizabeth Swift, Elizabeth Swift Kentucky Agricultural Experiment Station, Lexington, Kentucky Search for other works by this author on: Oxford Academic Google Scholar Rodney Hays, Rodney Hays Kentucky Agricultural Experiment Station, Lexington, Kentucky Search for other works by this author on: Oxford Academic Google Scholar Z F Kaufman Z F Kaufman Kentucky Agricultural Experiment Station, Lexington, Kentucky Search for other works by this author on: Oxford Academic Google Scholar Journal of Association of Official Agricultural Chemists, Volume 35, Issue 3, 1 August 1952, Pages 764–767, https://doi.org/10.1093/jaoac/35.3.764 Published: 10 February 2020

Swift

Phosphoric acid

10.1093/jaoac/35.3.764

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Citations (1)

Functional-Group-Tolerant, Nickel-Catalyzed Cross-Coupling Reaction for Enantioselective Construction of Tertiary Methyl-Bearing Stereocenters

Journal of the American Chemical Society (2013)

Hanna M. Wisniewska Elizabeth C. Swift Elizabeth R. Jarvo

The first Negishi nickel-catalyzed stereospecific cross-coupling reaction of secondary benzylic esters is reported. A series of traceless directing groups is evaluated for ability to promote cross-coupling with dimethylzinc. Esters with a chelating thioether derived from commercially available 2-(methylthio)acetic acid are most effective. The products are formed in high yield and with excellent stereospecificity. A variety of functional groups are tolerated in the reaction including alkenes, alkynes, esters, amines, imides, and O-, S-, and N-heterocycles. The utility of this transformation is highlighted in the enantioselective synthesis of a retinoic acid receptor agonist and a fatty acid amide hydrolase inhibitor.

Negishi coupling

Stereocenter

Stereospecificity

Amide

Coupling reaction

Thioether

Functional group

10.1021/ja4034999

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Citations (128)

Scalable Synthesis of ABBV-105 Enabled by Suzuki Coupling with Low Pd Loading, Ru-Catalyzed Asymmetric Hydrogenation, and Acylation Using Impinging Jet

Organic Process Research & Development (2024)

Benoit Cardinal‐David Shashank Shekhar Eric M. Phillips Elizabeth C. Swift Brian Kotecki

Evolution of a synthetic process to prepare ABBV-105, a Bruton's tyrosine kinase (BTK)-inhibitor, on multikilogram scale is described. The first-generation route utilized chiral resolution of the penultimate intermediate (7). Either Bartoli or Leimgruber–Batcho indole synthesis was used to prepare the key intermediate, indole boronate ester (23). As the demand for the API increased, the first-generation route was found to be low-yielding and expensive. It required column chromatography, had multiple alerting structures from the mutagenic impurity assessment, and suffered from lack of robustness. In the second-generation route a novel Ru-catalyzed asymmetric hydrogenation of 1,2,5,6-tetrahydropyridine (21) was developed to establish the stereocenter. Compound 21 was accessed via Suzuki coupling of 23, prepared by Friedel–Crafts acylation, with vinyl bromide (24) in the presence of very low loading of a Pd catalyst (0.15 mol % Pd). Finally, the penultimate intermediate (7) was coupled with acryloyl chloride using an impinging jet to prepare the API. Detailed kinetic and mechanistic work was conducted to control the persistent impurities formed in the API step. The second-generation route was robust, chromatography-free and high-yielding with low mutagenic liability.

10.1021/acs.oprd.4c00117

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Citations (1)

Synthesis of Highly Functionalized 4-Iodo-7-azaindazoles via Condensation/Diels–Alder/Retro-Diels–Alder Cyclization of Iodoalkynones and 2-Hydrazineylpyrimidines

Organic Letters (2023)

Elizabeth C. Swift Zachary S. Sales Dongpei Wu Anastassia Matviitsuk Daniel J. Pippel

A method for the preparation of highly functionalized 4-iodo-7-azaindazoles is reported. These valuable heterocycles are synthesized via condensation of 2-hydrazineylpyrimidines with various iodoalkynones followed by Diels-Alder/retro-Diels-Alder cyclization. The method is general to the formation of products with a variety of C3, C5, and C6 substituents while preserving the C4 iodide functional handle for further late-stage functionalization. The utility of this transformation is demonstrated through the rapid synthesis of several bioactive azaindazole targets.

Diels–Alder reaction

Surface Modification

10.1021/acs.orglett.3c03481

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Citations (2)

Heterogeneous catalysis with nickel-on-graphite (Ni/C_g)

Organic & Biomolecular Chemistry (2007)

T.A. Butler Elizabeth C. Swift Bruce H. Lipshutz

Impregnation of nickel(II) onto graphite, upon reduction in situ, leads to a reagent that catalyzes both C-H and C-C bond formations between aryl halides, or aryl pseudo-halides, and various organometallics. Cross-couplings, most notably with tosylates, can lead to either reduced aromatics, biaryls, or styrenes as products under the influence of Ni/Cg. The catalyst is inexpensive, non-pyrophoric, and reusable.

10.1039/b714600k

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Citations (28)

Asymmetric transition metal-catalyzed cross-coupling reactions for the construction of tertiary stereocenters

Tetrahedron (2013)

Elizabeth C. Swift Elizabeth R. Jarvo

Stereocenter

Annulation

Coupling reaction

Organic Synthesis

Suzuki reaction

10.1016/j.tet.2013.05.001

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Citations (118)

C−C Bond Formation Catalyzed Heterogeneously by Nickel-on-Graphite (Ni/C_g)

Organic Letters (2008)

Bruce H. Lipshutz T.A. Butler Elizabeth C. Swift

Inexpensive nickel(II) mounted on graphite (Ni/Cg) can be easily activated and used to heterogeneously catalyze cross-couplings involving aryl halides/tosylates with boronic acids, vinylalanes, and vinylzirconocenes. Comparisons are made with the charcoal analogue, Ni/C, and some unusual chemoselectivities between these catalysts have been uncovered.

Charcoal

10.1021/ol702453q

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Citations (59)

CCDC 1979866: Experimental Crystal Structure Determination

The Cambridge Structural Database (2020)

Elizabeth C. Swift Shashank Shekhar Brian Kotecki

10.5517/ccdc.csd.cc24g6nh

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Citations (0)