The development of powerful new methods for the generation of carbon-carbon bonds has an impact on a wide array of disciplines that require the synthesis of organic compounds (e.g., biological chemistry, pharmaceutical chemistry, and biology). Transition metals can catalyze carbon-carbon bond-forming processes, such as cross-couplings of organic electrophiles and nucleophiles, that would otherwise be difficult or impossible to achieve. During the next grant period, this program will pursue a largely unexplored dimension of cross-coupling reactions-processes that employ alkyl electrophiles as substrates. Efforts will focus on the development of versatile catalysts, including chiral catalysts, for a wide range of powerful bond-forming processes. Such reactions have the potential to simultaneously generate a carbon-carbon bond and to define up to two new stereocenters. Mechanistic studies will play an important role in this project, since an improved understanding of metal-based reactivity could facilitate catalyst development. This research area offers an exciting opportunity to have a substantial impact on synthetic chemistry, as well as to enrich our understanding of once-unexpected chemical reactivity.
In order to probe many biological questions and to develop new therapeutic compounds, there is a need to be able to synthesize organic molecules efficiently and to control the chirality ("handedness") of the target compounds. This proposal is directed at addressing both of these challenges.
|Zuo, Zhiwei; Cong, Huan; Li, Wei et al. (2016) Enantioselective Decarboxylative Arylation of Î±-Amino Acids via the Merger of Photoredox and Nickel Catalysis. J Am Chem Soc 138:1832-5|
|Chu, Crystal K; Liang, Yufan; Fu, Gregory C (2016) Silicon-Carbon Bond Formation via Nickel-Catalyzed Cross-Coupling of Silicon Nucleophiles with Unactivated Secondary and Tertiary Alkyl Electrophiles. J Am Chem Soc 138:6404-7|
|Liang, Yufan; Fu, Gregory C (2015) Nickel-Catalyzed Alkyl-Alkyl Cross-Couplings of Fluorinated Secondary Electrophiles: A General Approach to the Synthesis of Compounds having a Perfluoroalkyl Substituent. Angew Chem Int Ed Engl 54:9047-51|
|Liang, Yufan; Fu, Gregory C (2015) Stereoconvergent Negishi Arylations of Racemic Secondary Alkyl Electrophiles: Differentiating between a CF3 and an Alkyl Group. J Am Chem Soc 137:9523-6|
|Schley, Nathan D; Fu, Gregory C (2014) Nickel-catalyzed Negishi arylations of propargylic bromides: a mechanistic investigation. J Am Chem Soc 136:16588-93|
|Liang, Yufan; Fu, Gregory C (2014) Catalytic asymmetric synthesis of tertiary alkyl fluorides: Negishi cross-couplings of racemic Î±,Î±-dihaloketones. J Am Chem Soc 136:5520-4|
|Choi, Junwon; MartÃn-Gago, Pablo; Fu, Gregory C (2014) Stereoconvergent arylations and alkenylations of unactivated alkyl electrophiles: catalytic enantioselective synthesis of secondary sulfonamides and sulfones. J Am Chem Soc 136:12161-5|
|Cong, Huan; Fu, Gregory C (2014) Catalytic enantioselective cyclization/cross-coupling with alkyl electrophiles. J Am Chem Soc 136:3788-91|
|Cordier, Christopher J; Lundgren, Rylan J; Fu, Gregory C (2013) Enantioconvergent cross-couplings of racemic alkylmetal reagents with unactivated secondary alkyl electrophiles: catalytic asymmetric Negishi Î±-alkylations of N-Boc-pyrrolidine. J Am Chem Soc 135:10946-9|
|Zultanski, Susan L; Fu, Gregory C (2013) Nickel-catalyzed carbon-carbon bond-forming reactions of unactivated tertiary alkyl halides: Suzuki arylations. J Am Chem Soc 135:624-7|
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