The University of Osaka · Chemistry
Professor Renhua Qiu's research lab specializes in the development of sustainable and efficient catalytic methodologies in organic synthesis, with a strong focus on transition metal and organometallic catalysis. The lab pioneers innovative C–H bond functionalization strategies, particularly for the selective chalcogenation of nitrogen-containing heterocycles such as carbazoles, indoles, and quinolones, using palladium and copper catalysts. A key direction involves designing reusable, air-stable, and highly selective organometallic Lewis acid catalysts—especially bismuth-based systems—that function efficiently in aqueous media, enabling green and diastereoselective transformations. The lab also explores practical, one-pot syntheses of bioactive molecules, such as 3,3'-diindolylmethanes, with demonstrated anticancer properties.
Figures are computed from collected data and may differ slightly.
Palladium catalyzes the intermolecular chalcogenation of carbazole, 2-phenylpyridine, benzo[h]quinolone, and indole derivatives with disulfides and diselenides via selective C-H bond cleavage, providing a convenient route to thio and selenoethers.
An air-stable cationic organobismuth complex was successfully synthesized and found to show high catalytic efficiency in the direct diastereoselective Mannich reaction in water.
A concise, one-step route to produce 3,3'-diindolylmethanes (DIMs) from simple indoles and ketones or aldehydes is reported. The key step is the ready formation of indole derivatives that involves the in situ conversion of CF<sub>3</sub>SO<sub>2</sub>Na reagent to ·CF<sub>3</sub> under oxygen or air (1.0 atm) and UV irradiation. It is disclosed that most of the obtained DIMs show anticancer activities in human bladder cancer cell lines EJ and T24.
Organometallic Lewis acids play an important role in modern organic synthesis. How to design and synthesize highly efficient and recyclable organometallic Lewis acid catalysts that can be conveniently applied in chemical reactions are key issues for sustainable synthetic processes. In general, stronger acidity means higher catalytic activity for organometallic Lewis acids. However, with the rise in acidity, the compound becomes more susceptible to hydrolysis and cannot be recycled. Simultaneous
Cu-mediated direct thiolation of carbazole derivatives with disulfides <italic>via</italic> C–H bond cleavage to give diaryl and alkyl aryl sulfides which easily extends to the synthesis of thioethers with a benzo[<italic>h</italic>]quinolone, 2-phenylquinoline or indole moiety in satisfactory yields.
Abstract An air‐stable cationic organobismuth perfluorooctanesulfonate possessing both acidic and basic characters was synthesized, and showed high catalytic activity, diastereoselectivity, stability, and reusability in the one‐pot synthesis of ( E )‐α,β‐unsaturated ketones through highly selective crossed condensation of ketones and aldehydes in water.
Strong Lewis acids of air-stable metallocene bis(perfluorooctanesulfonate)s [M(Cp)(2)][OSO(2)C(8)F(17)](2)⋅nH(2)O⋅THF (M = Zr (2 a⋅3 H(2)O⋅THF), M = Ti (2 b⋅2 H(2)O⋅THF)) were synthesized by the reaction of [M(Cp)(2)]Cl(2) (M = Zr (1 a), M = Ti (1 b)) with nBuLi and C(8)F(17)SO(3)H (2 equiv) or with C(8)F(17)SO(3)Ag (2 equiv). The hydrate numbers (n) of these complexes were variable, changing from 0 to 4 depending on conditions. In contrast to well-known metallocene triflates, these complexes su
A Ni-catalyzed oxidative C-H/C-H cross-dehydrogenative coupling (CDC) reaction was developed for constructing various highly functionalized alkyl (aryl)-substituted thiophenes. This method employs thiophenes and aliphatic (aromatic) amides that contain an 8-aminoquinoline as a removable directing group in the presence of a silver oxidant. The approach enables the facile one-step synthesis of substituted thiophenes with high functional group compatibility via double C-H bond cleavage without affe
The catalyst system that comprises an air-stable bifunctional Lewis acidic/basic organobismuth complex and [Bmim]BF4 is highly efficient in the cross-condensation of aldehydes with ketones. Through switching the reaction from homogeneous to heterogeneous, the system shows facile separation ability and facile reusability.
In the direct Mannich reaction and synthesis of α,β-unsaturated ketones, the use of organobismuth complexes as catalysts leads to high diastereoselectivity and products of single trans conformation. In this paper, we illustrate the relationship between structure and catalytic activity as well as diastereoselectivity of organobismuth complexes having a 5,6,7,12-tetrahydrodibenz [c,f][1,5]thiobismocine framework as well as bearing a butterfly-shaped sulfur-bridged ligand and tunable anions. With t
A Cu-catalyzed protocol for cross-dehydrogenative coupling of benzofuranones with quinolines, indoles, carbazoles, and thiophene, which furnishes highly functionalized 3,3-diaryl benzofuranones bearing a three aryl quaternary carbon center at the C3 position in good yields, has been developed. A radical mechanism is proposed.
Air-stable Lewis acidic micro2-hydroxy bridged binuclear complex of zirconocene pentafluorophenylsulfonate was successfully synthesized and found to show high catalytic efficiency in chemoselective allylation of carbonyl compounds with tetraallyltin in aqueous methanol media.
The utilization of organoantimony and organobismuth complexes in CO<sub>2</sub>fixation is reviewed in this article.
The surface functionality of Au38S2(SAdm)20 nanoclusters (-SAdm = adamantanethiolate) in the presence of α-, β-, and γ-cyclodextrins (CDs) is studied. The supramolecular chemistry and host-guest interactions of CDs and the protecting ligands of nanoclusters are investigated using UV-vis and NMR spectroscopies, MALDI mass spectrometry, and molecular dynamics simulations. In contrast to α- and γ-CDs, the results show that β-CDs are capable of efficiently chemisorbing onto the Au38S2(SAdm)20 nanocl
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