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 Our research combines techniques of organic synthesis, physical organic chemistry and organometallic chemistry to devise catalytic processes of use to organic synthesis. In this way we invent or develop new processes, determine how they proceed and apply them in a synthetically interesting context. For instance, we might use them to develop a new synthetic method, or apply them in the total synthesis of a structurally or pharmaceutically interesting molecule. In recent years, we have been interested in the development of catalytic processes for the formation of carbon-carbon and carbon-heteroatom bonds. For example, we reported the first examples of Suzuki Coupling processes that utilize unactivated aryl chlorides as well as the first examples of these processes that can be carried out at room temperature. We have furthermore developed methods for the coupling of extremely hindered substrates as well as an asymmetric version of this reaction. We have been the leader in the development of methods for the arylation and vinylation of carbonyl enolates. We have also developed asymmetric versions of these powerful reactions. In recent years, carbon-nitrogen bond-forming processes have become among the most important reactions in the pharmaceutical industry. Our group has been at the forefront of this work and we have developed the most general methods to accomplish this important task. This work has included the use of both palladium and copper catalysts. Our methods have been widely embraced by practicing synthetic chemists and have been used in the preparation of a number of polyfunctionalized and/or medicinally interesting compounds. Our work involves a great deal of organometallic chemistry, particularly with respect to ligand development and kinetic studies of these processes. In addition to carbon-nitrogen bond-forming processes, we have also developed methods for the formation of carbon-oxygen, carbon-sulfur and carbon-halogen bonds. An additional longstanding area
of interest in our group has been in the development of new catalysts
for the asymmetric reduction of prochiral
molecules. In recent years we have focused on the use of copper catalysts
for the conjugate reduction of α,β-unsaturated carbonyl compounds.
Wolfe, J.P.; Buchwald, S.L. "Scope and Limitations of the Pd/BINAP-Catalyzed Amination of Aryl Bromides." J. Org. Chem. 2000, 65, 1144. Yin, J.; Buchwald, S.L. "A Catalytic Asymmetric Suzuki Coupling fo rthe Synthesis of Axially Chiral Biaryl Compounds." J. Am. Chem. Soc. 2000, 122, 12051. Kuwabe, S.-I.; Torraca, K.E.; Buchwald, S.L. "Palladium-Catalyzed Intramolecular C-O Bond Formation." J. Am. Chem. Soc. 2001, 123, 12202. Hamada, T; Chieffi, A.; Åhman, J.; Buchwald, S.L. "An Improved Catalyst for the Asymmetric Arylation of Ketone Enolates." J. Am. Chem. Soc. 2002, 124, 1261. Yin, J.; Rainka, M.P.; Zhang X.-X.; Buchwald, S.L. "A Highly Active Suzuki Catalyst for the Synthesis of Sterically Hindered Biaryls: Novel Ligand Coordination." J. Am. Chem. Soc. 2002, 124, 1162. Jurkauskas, V; Buchwald, S.L. “Dynamic Kinetic Resolution via Asymmetric Conjugate Reduction: Enantio- and Diastereoselective Synthesis of 2,4-Dialkyl Cyclopentanones.” J. Am. Chem. Soc. 2002, 124, 2892. Klapars, A.; Huang, X.; Buchwald, S.L. "A General and Efficient Copper Catalyst for the Amidation of Aryl Halides." J. Am. Chem. Soc. 2002, 124, 7421. Singh, U.K.; Strieter, E.R.; Blackmond, D.I.; Buchwald, S.L. “Mechanistic Insights into the Pd(BINAP)-Catalyzed Amination of Aryl Bromides: Studies Under Synthetically Relevant Conditions.” J. Am. Chem. Soc. 2002, 124, 14104. Klapars, A.; Buchwald, S.L. “Copper-Catalyzed Halogen Exchange in Aryl Halides: An Aromatic Finkelstein Reaction." J. Am. Chem. Soc. 2002, 124, 14844. |
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