The ability to prepare functionalized organic molecules rationally and predictably, whether individually or in libraries, is central to organic synthesis, medicinal chemistry and the pharmaceutical industry.
The aims of this work are to develop new and/or improved methods for the formation of carbon-nitrogen and carbon-oxygen bonds. Included in this work is the development of new strategies and techniques for the preparation of complex heterocycles, which are the building blocks of medicinal chemistry and the pharmaceutical industry, via cross-coupling methodology. Further, information gained from this work will help to understand the mechanism of the processes that are being developed in order to increase the rate of improvement of the techniques that we are studying. The development of new methods for organic synthesis is key to the development of the field of organic chemistry as a whole. These reactions are of critical importance to the pharmaceutical industry. Cross-coupling methods for carbon-heteroatom bond formation are regularly used by those in the pharmaceutical industry for the preparation of analogues with increased potency and reduced side effects. Moreover, the methods can be employed for the preparation of quantities of new substances for preclinical and clinical testing and for the actual manufacture of a pharmaceutical agent. The techniques that are being developed allow for these important functions to be carried out in a more rapid and efficient fashion than previously possible. Moreover, they allow for the preparation of new substances, which have previously been inaccessible. These new compounds have the possibilities of having physiological properties of great importance in medicinal chemistry and the pharmaceutical industry. Further these techniques are used by researchers in both academia and industry in a variety of areas of bioorganic and materials research including in the formation of new sensory materials.
The cross-coupling methods we are developing for carbon-heteroatom bond formation are regularly used by those in the pharmaceutical industry for the preparation of analogues with increased potency and reduced side effects. Moreover, the methods can be employed for the preparation of quantities of new substances for preclinical and clinical testing and for the actual manufacture of a pharmaceutical agent.
|Lu, Gang; Liu, Richard Y; Yang, Yang et al. (2017) Ligand-Substrate Dispersion Facilitates the Copper-Catalyzed Hydroamination of Unactivated Olefins. J Am Chem Soc 139:16548-16555|
|Olsen, Esben P K; Arrechea, Pedro L; Buchwald, Stephen L (2017) Mechanistic Insight Leads to a Ligand Which Facilitates the Palladium-Catalyzed Formation of 2-(Hetero)Arylaminooxazoles and 4-(Hetero)Arylaminothiazoles. Angew Chem Int Ed Engl 56:10569-10572|
|Zhou, Yujing; Bandar, Jeffrey S; Buchwald, Stephen L (2017) Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates. J Am Chem Soc 139:8126-8129|
|Ingoglia, Bryan T; Buchwald, Stephen L (2017) Oxidative Addition Complexes as Precatalysts for Cross-Coupling Reactions Requiring Extremely Bulky Biarylphosphine Ligands. Org Lett 19:2853-2856|
|Gribble Jr, Michael W; Pirnot, Michael T; Bandar, Jeffrey S et al. (2017) Asymmetric Copper Hydride-Catalyzed Markovnikov Hydrosilylation of Vinylarenes and Vinyl Heterocycles. J Am Chem Soc 139:2192-2195|
|Wang, Haoxuan; Yang, Jeffrey C; Buchwald, Stephen L (2017) CuH-Catalyzed Regioselective Intramolecular Hydroamination for the Synthesis of Alkyl-Substituted Chiral Aziridines. J Am Chem Soc 139:8428-8431|
|Corcoran, Emily B; Pirnot, Michael T; Lin, Shishi et al. (2016) Aryl amination using ligand-free Ni(II) salts and photoredox catalysis. Science 353:279-83|
|King, Sandra M; Buchwald, Stephen L (2016) Development of a Method for the N-Arylation of Amino Acid Esters with Aryl Triflates. Org Lett 18:4128-31|
|Ruiz-Castillo, Paula; Buchwald, Stephen L (2016) Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions. Chem Rev 116:12564-12649|
|Friis, Stig D; Pirnot, Michael T; Buchwald, Stephen L (2016) Asymmetric Hydroarylation of Vinylarenes Using a Synergistic Combination of CuH and Pd Catalysis. J Am Chem Soc 138:8372-5|
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