Daniel J. Weix

Daniel J. Weix

Associate Professor of Chemistry

Ph.D. 2005, University of California, Berkeley

Organic Methods Development, Organometallic Chemistry, and Catalysis

The research in my group focuses on the development of new catalytic methods for organic synthesis. While many new synthetic methods are developed every year, few ever become widely used outside the laboratory they were developed in. The reason for this is often that the overall synthetic scheme is just less efficient than what was already available – starting materials or catalysts are difficult to handle, expensive, or both. In order to create reactions that will find immediate use in academia and industry, we are developing new couplings of readily available starting materials. Integral to the development process are the study of the proposed reaction mechanisms and the synthesis of potential catalytic intermediates.

Even the relatively efficient process syntheses of active pharmaceutical ingredients require, on average, eight steps. To further improve the overall efficiency at this stage requires methods that avoid purification and isolation steps. Many chemists use “one-pot” procedures to conduct two or more reactions sequentially in a single flask. A potentially more powerful strategy is running two or more reactions concurrently in a single flask, dubbed “concurrent tandem catalysis.” Inspired by nature, my group seeks to create abiotic megasynthases that will perform a programmed series of reactions and allow for true multistep synthesis in a single flask. To accomplish this goal, we will draw upon the tools of various chemistry disciplines (bioorganic, supermolecular, organic, and inorganic) to create and study these synthases.

Selected Publications

Everson, D. A.; Weix, D. J.  "Cross-Electrophile Coupling: Principles of Reactivity and Selectivity,"  J. Org. Chem.  2014794793-4798. Invited Contribution.. http://dx.doi.org/10.1021/jo500507s
Zhao, Y.; Weix, D. J.  "Nickel-Catalyzed Regiodivergent Opening of Epoxides with Aryl Halides: Co-Catalysis Controls Regioselectivity,"  J. Am. Chem. Soc.  201413648-51. http://dx.doi.org/10.1021/ja410704d
Chen, C.; Dugan, T. R.; Brennessel, W. W.; Weix, D. J.; Holland, P. L.  "Z-Selective Alkene Isomerization by High-Spin Cobalt(II) Complexes,"  J. Am. Chem. Soc.  2014136945-955. http://dx.doi.org/10.1021/ja408238n
Everson, D. A.; Buonomo, J. A.; Weix, D. J.  "Nickel-catalyzed cross-electrophile coupling of 2-chloropyridines with alkyl bromides,"  Synlett  201425233-238. http://dx.doi.org/10.1055/s-0033-1340151
Biswas, S.; Weix, D. J.  "Mechanism and Selectivity in Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Halides with Alkyl Halides,"  J. Am. Chem. Soc.  201313516192–16197. http://dx.doi.org/10.1021/ja407589e
Buonomo, J. A.; Everson, D. A.; Weix, D. J.  "Substituted 2,2’-bipyridines by nickel-catalysis: 4,4’-di-tert-butyl-2,2’-bipyridine,"  Synthesis  2013453099-3102. http://dx.doi.org/10.1055/s-0033-1338520
Shrestha, R.; Dorn, S. C. M.; Weix, D. J.  "Nickel-Catalyzed Reductive Conjugate Addition Via Allylnickel Intermediates,"  J. Am. Chem. Soc.  2013135751-762. http://dx.doi.org/10.1021/ja309176h
Everson, D. A.; George, D. T.; Weix, D. J.; Buergler, J. F.; Wood, J. L.  "Nickel-Catalyzed Cross-Coupling of Aryl Halides with Alkyl Halides: Ethyl 4-(4-(4-methylphenylsulfonamido)phenyl)butanoate,"  Org. Synth.  201390200-214. http://dx.doi.org/10.15227/orgsyn.090.0200
Anka-Lufford, L. L.; Prinsell, M. R.; Weix, D. J.  "Selective Cross-Coupling of Organic Halides with Allylic Acetates,"  J. Org. Chem.  2012779989-10000. http://dx.doi.org/10.1021/jo302086g
Everson, D. A.; Jones, B. A.#; Weix, D. J.*  "Replacing conventional carbon nucleophiles with electrophiles: nickel-catalyzed reductive alkylation of aryl bromides and chlorides,"  J. Am. Chem. Soc.  20121346146-6159. http://dx.doi.org/10.1021/ja301769r
Wotal, A. C.; Weix, D. J.  "Synthesis of Functionalized Dialkyl Ketones from Carboxylic Acid Derivatives and Alkyl Halides,"  Org. Lett.  2012141476-1479. http://dx.doi.org/10.1021/ol300217x
Shrestha, R., Weix, D. J.  "Reductive Conjugate Addition of Haloalkanes to Enones To Form Silyl Enol Ethers,"  Org. Lett.  2011132766-2769. http://dx.doi.org/10.1021/ol200881v
Prinsell, M. R., Everson, D. A., Weix, D. J.  "Nickel-Catalyzed, Sodium Iodide-Promoted Reductive Dimerization of Alkyl Halides, Alkyl Pseudohalides, and Allylic Acetates,"  Chem. Commun.  2010465743-5745. http://dx.doi.org/10.1039/C0CC01716G
Everson, D. A., Shrestha, R., Weix, D. J.  "Nickel-Catalyzed Reductive Cross-Coupling of Aryl Halides with Alkyl Halides,"  J. Am. Chem. Soc.  2010132920-921. http://dx.doi.org/10.1021/ja9093956
Weix, D. J., Markovic, D., Ueda, M., Hartwig, J. F.  "Direct, Intermolecular, Enantioselective, Iridium-Catalyzed Allylation of Carbamates to Form Carbamate-Protected, Branched Allylic Amines,"  Org. Lett.  2009112944-2947.
Pouy, M. J., Leitner, A., Weix, D. J., Ueno, S. and Hartwig, J. F.  "Enantioselective Iridium-Catalyzed Allylic Amination Using Ammonia and Convenient Ammonia Surrogates,"  Org. Lett.  200793949-3952.
Weix, D. J., Hartwig, J. F.  "Regioselective and Enantioselective Iridium-Catalyzed Allylation of Enamines,"  J. Am. Chem. Soc.  20071297720-7721.
Weix, D. J., Shi, Y., Ellman, J. A.  "Diastereoselective and Enantioselective Rh(I)-Catalyzed Additions of Arylboronic Acids to N-tert-Butanesulfinyl and N-Diphenylphosphinoyl Aldimines,"  J. Am. Chem. Soc.  20051271092-1093.
Weix, D. J., Ellman, J. A., Wang, X., Curran, D. P.   "(RS)-(+)-2-methyl-2-propanesulfinamide,"  Org. Synth.  200582157-165.
Weix, D. J., Ellman, J. A.   "Improved Synthesis of tert-Butanesulfinamide Suitable for Large-Scale Production,"  Org. Lett.  200351317-1320.
Weix, D. J., Dreher, S. D., Katz, T. J.  "[5]HELOL Phosphite: A Helically Grooved Sensor of Remote Chirality,"  J. Am. Chem. Soc.  200012210027-10032.
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Professor Weix's Contact Information...

Office: Hutchison 412
Phone: (585) 275-8383

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