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.
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.
|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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