We are engaged in the systematic efforts to exploit catalytic carbon?carbon (C?C) bond activation for developing new, general and synthetically useful methods. Our objective, in the proposed funding period, is to focus on C?C activation of ketones, as ketone moieties are ubiquitously found in feedstock chemicals, synthetic building blocks and bioactive compounds. Specifically, we will: (i) expand the scope and utilities with activation of strained ketones for constructing complex ring systems, (ii) enable new and broadly applicable transformations with unstrained ketones in an atom-economical fashion, and (iii) explore a new activation mode that can shift the paradigm for ketone activation. The research proposed is expected to simplify synthesis through new strategic bond disconnections, allow for editing skeletons of complex molecules under redox-neutral conditions, and offer a byproduct-free approach to access organic building blocks.

Public Health Relevance

Small molecules of medicinal interests generally contain carbon-carbon (C?C) bonds in their skeletons, thus methods that selectively edit specific C?C bonds are highly desirable as syntheses of biologically important compounds could be simplified or streamlined. However, broadly applicable C?C activation approaches remain largely elusive. The outlined proposal exploits several unique modes of transition-metal-mediated C?C bond activation discovered in our laboratory in developing a suite of catalytic methods that are useful for constructing complex molecules.

National Institute of Health (NIH)
National Institute of General Medical Sciences (NIGMS)
Research Project (R01)
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Synthetic and Biological Chemistry B Study Section (SBCB)
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Yang, Jiong
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University of Chicago
Schools of Arts and Sciences
United States
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Xia, Ying; Wang, Jianchun; Dong, Guangbin (2018) Suzuki-Miyaura Coupling of Simple Ketones via Activation of Unstrained Carbon-Carbon Bonds. J Am Chem Soc 140:5347-5351
Zhu, Zixi; Li, Xinghan; Chen, Sicong et al. (2018) Cobalt-Catalyzed Intramolecular Alkyne/Benzocyclobutenone Coupling: C-C Bond Cleavage via a Tetrahedral Dicobalt Intermediate. ACS Catal 8:845-849
Deng, Lin; Jin, Likun; Dong, Guangbin (2018) Fused-Ring Formation by an Intramolecular ""Cut-and-Sew"" Reaction between Cyclobutanones and Alkynes. Angew Chem Int Ed Engl 57:2702-2706
Rong, Zi-Qiang; Lim, Hee Nam; Dong, Guangbin (2018) Intramolecular Acetyl Transfer to Olefins by Catalytic C-C Bond Activation of Unstrained Ketones. Angew Chem Int Ed Engl 57:475-479
Chen, Peng-Hao; Billett, Brent A; Tsukamoto, Tatsuhiro et al. (2017) ""Cut and Sew"" Transformations via Transition-Metal-Catalyzed Carbon-Carbon Bond Activation. ACS Catal 7:1340-1360
Xia, Ying; Wang, Jianbo; Dong, Guangbin (2017) Distal-Bond-Selective C-C Activation of Ring-Fused Cyclopentanones: An Efficient Access to Spiroindanones. Angew Chem Int Ed Engl 56:2376-2380
Zeng, Rong; Chen, Peng-Hao; Dong, Guangbin (2016) Efficient Benzimidazolidinone Synthesis via Rhodium-Catalyzed Double-Decarbonylative C-C Activation/Cycloaddition between Isatins and Isocyanates. ACS Catal 6:969-973
Chen, Peng-Hao; Dong, Guangbin (2016) Cyclobutenones and Benzocyclobutenones: Versatile Synthons in Organic Synthesis. Chemistry 22:18290-18315
Deng, Lin; Xu, Tao; Li, Hongbo et al. (2016) Enantioselective Rh-Catalyzed Carboacylation of C?N Bonds via C-C Activation of Benzocyclobutenones. J Am Chem Soc 138:369-74
Xia, Ying; Lu, Gang; Liu, Peng et al. (2016) Catalytic activation of carbon-carbon bonds in cyclopentanones. Nature 539:546-550

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