Alternative Pathways to α,β-unsaturated Ketones Via Direct Oxidative Coupling Transformation Using Sr-doped LaCoO Perovskite Catalyst

Overview

Journal R Soc Open Sci

Specialty Science

Date 2019 Dec 13

PMID 31827863

Authors

Khang H Trinh

Son H Doan

Tien V Huynh

Phuong H Tran

Diep N Pham

Minh-Vien Le

Tung T Nguyen

Nam T S Phan

Affiliations

Soon will be listed here.

Abstract

A strontium-doped lanthanum cobaltite perovskite material was prepared, and used as a recyclable and effective heterogeneous catalyst for the direct oxidative coupling of alkenes with aromatic aldehydes to produce α,β-unsaturated ketones. The reaction afforded high yields in the presence of di--butylperoxide as oxidant. Single oxides or salts of strontium, lanthanum and cobalt, and the undoped perovskite offered a lower catalytic activity than the strontium-doped perovskite. Benzaldehyde could be replaced by benzyl alcohol, dibenzyl ether, 2-oxo-2-phenylacetaldehyde, 2-bromoacetophenone or (dimethoxymethyl) benzene in the oxidative coupling reaction with alkenes. To our best knowledge, reactions between these starting materials with alkenes are new and unknown in the literature.

References

Jung M, Ji S, Kim G, Seok S . Perovskite precursor solution chemistry: from fundamentals to photovoltaic applications. Chem Soc Rev. 2019; 48(7):2011-2038. DOI: 10.1039/c8cs00656c. View

Wang F, Yu S, Li X . Transition metal-catalysed couplings between arenes and strained or reactive rings: combination of C-H activation and ring scission. Chem Soc Rev. 2016; 45(23):6462-6477. DOI: 10.1039/c6cs00371k. View

Pan K, Pan G, Chong S, Chang M . Removal of VOCs from gas streams with double perovskite-type catalysts. J Environ Sci (China). 2018; 69:205-216. DOI: 10.1016/j.jes.2017.10.012. View

Wang X, Huang K, Yuan L, Xi S, Yan W, Geng Z . Activation of Surface Oxygen Sites in a Cobalt-Based Perovskite Model Catalyst for CO Oxidation. J Phys Chem Lett. 2018; 9(15):4146-4154. DOI: 10.1021/acs.jpclett.8b01623. View

Jung W, Lim K, Kim J, Lee M, Hong S . Synthesis of Pb-substituted LaCoO3 nanoparticles by microwave process and their photocatalytic activity under visible light irradiation. J Nanosci Nanotechnol. 2013; 13(9):6160-4. DOI: 10.1166/jnn.2013.7639. View

Kuga T, Sasano Y, Iwabuchi Y . IBX as a catalyst for dehydration of hydroperoxides: green entry to α,β-unsaturated ketones via oxygenative allylic transposition. Chem Commun (Camb). 2018; 54(7):798-801. DOI: 10.1039/c7cc08957k. View

Choi J, Jang B, Cho N, Park J, Yeon S, Ju E . Synthesis of a series of unsaturated ketone derivatives as selective and reversible monoamine oxidase inhibitors. Bioorg Med Chem. 2015; 23(19):6486-96. DOI: 10.1016/j.bmc.2015.08.012. View

Liu Q, Jackstell R, Beller M . Oxidative catalytic coupling reactions: selective formation of C-C and C-X bonds using radical processes. Angew Chem Int Ed Engl. 2013; 52(52):13871-3. DOI: 10.1002/anie.201307865. View

Wang J, Liu C, Yuan J, Lei A . Copper-catalyzed oxidative coupling of alkenes with aldehydes: direct access to α,β-unsaturated ketones. Angew Chem Int Ed Engl. 2013; 52(8):2256-9. DOI: 10.1002/anie.201208920. View

10.

Dukkanci M . Sono-photo-Fenton oxidation of bisphenol-A over a LaFeO perovskite catalyst. Ultrason Sonochem. 2017; 40(Pt B):110-116. DOI: 10.1016/j.ultsonch.2017.04.040. View

11.

Luo S, Zhang N, Wang Z, Yan H . Enantioselective addition of selenosulfonates to α,β-unsaturated ketones. Org Biomol Chem. 2018; 16(16):2893-2901. DOI: 10.1039/c8ob00359a. View

12.

Liu L, Zhang H, Jia J, Sun T, Sun M . Direct Molten Polymerization Synthesis of Highly Active Samarium Manganese Perovskites with Different Morphologies for VOC Removal. Inorg Chem. 2018; 57(14):8451-8457. DOI: 10.1021/acs.inorgchem.8b01125. View

13.

Wang W, Tade M, Shao Z . Research progress of perovskite materials in photocatalysis- and photovoltaics-related energy conversion and environmental treatment. Chem Soc Rev. 2015; 44(15):5371-408. DOI: 10.1039/c5cs00113g. View

14.

Arandiyan H, Wang Y, Sun H, Rezaei M, Dai H . Ordered meso- and macroporous perovskite oxide catalysts for emerging applications. Chem Commun (Camb). 2018; 54(50):6484-6502. DOI: 10.1039/C8CC01239C. View

15.

Teng F, Sun S, Jiang Y, Yu J, Cheng J . Copper-catalyzed oxidative C(sp(3))-H/N-H coupling of sulfoximines and amides with simple alkanes via a radical process. Chem Commun (Camb). 2015; 51(27):5902-5. DOI: 10.1039/c5cc00839e. View

16.

Huang X, Zhao G, Wang G, Irvine J . Synthesis and applications of nanoporous perovskite metal oxides. Chem Sci. 2018; 9(15):3623-3637. PMC: 5944822. DOI: 10.1039/c7sc03920d. View

17.

Shi R, Niu H, Lu L, Lei A . Pd/Cu-Catalyzed aerobic oxidative aromatic C-H bond activation/N-dealkylative carbonylation towards the synthesis of phenanthridinones. Chem Commun (Camb). 2017; 53(11):1908-1911. DOI: 10.1039/c6cc08701a. View

18.

Song B, Xu B . Metal-catalyzed C-H functionalization involving isocyanides. Chem Soc Rev. 2016; 46(4):1103-1123. DOI: 10.1039/c6cs00384b. View

19.

Wei Y, Cheng Z, Lin J . An overview on enhancing the stability of lead halide perovskite quantum dots and their applications in phosphor-converted LEDs. Chem Soc Rev. 2018; 48(1):310-350. DOI: 10.1039/c8cs00740c. View

20.

Yang Z, Fonovic M, Verhelst S, Blum G, Bogyo M . Evaluation of alpha,beta-unsaturated ketone-based probes for papain-family cysteine proteases. Bioorg Med Chem. 2008; 17(3):1071-8. PMC: 2659416. DOI: 10.1016/j.bmc.2008.02.089. View