Tuning Regioselectivity of Wacker Oxidation in One Catalytic System: Small Change Makes Big Step

Hu, Kangfei; Ning, Xiaojuan; Qu, Jian‐Ping; Kang, Yan‐Biao

doi:10.1021/acs.joc.8b01547

Cited by 37 publications

(33 citation statements)

References 45 publications

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“…13 C NMR (101 MHz, CDCl 3 ) δ 202.1, 170.9, 167.6, 135.7, 134.3, 131.2, 130.3, 128.4, 128.3, 127.1, 126.7, 82.3, 49.1, 41.4, 39.3, 32.1, 23.6, 21.7. The spectral data were identical to those reported in the literature [65] …”

Section: Methodssupporting

confidence: 83%

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Micellar Catalysis for Sustainable Hydroformylation

et al. 2021

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It is here reported a fully sustainable and generally applicable protocol for the regioselective hydroformylation of terminal alkenes, using cheap commercially available catalysts and ligands, in mild reaction conditions (70 °C, 9 bar, 40 min). The process can take advantages from both micellar catalysis and microwave irradiation to obtain the linear aldehydes as the major or sole regioisomers in good to high yields. The substrate scope is largely explored as well as the application of hydroformylation in tandem with intramolecular hemiacetalization thus demonstrating the compatibility with a broad variety of functional groups. The reaction is efficient even in large scale and the catalyst and micellar water phase can be reused at least 5 times without any impact in reaction yields. The efficiency and sustainability of this protocol is strictly related to the in situ transformation of the aldehyde into the corresponding Bertagnini's salt that precipitates in the reaction mixture avoiding organic solvent mediated purification steps to obtain the final aldehydes as pure compounds.

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Section: Methodssupporting

confidence: 83%

“…The spectral data were identical to those reported in the literature. [65] The spectral data were identical to those reported in the literature. [67] 12-((tert-Butyldimethylsilyl)oxy)dodecanal (34).…”

Section: General Methods For the Hydroformylation Reactionsupporting

confidence: 81%

Micellar Catalysis for Sustainable Hydroformylation

et al. 2021

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“…The same group in 2018 modified the condition and developed a regioselective switchable aerobic Wacker‐Tsuji oxidation by solely switching the solvent from dry to wet alcohol. The reaction in dry t BuOH is aldehyde selective and follows anti‐Markovnikov's rule which is reverse in wet EtOH …”

Section: Outlines Of the Reactions Involving Tbnmentioning

confidence: 99%

“…The reactioni nd ry tBuOH is aldehyde selective and follows anti-Markovnikov's rule which is reverseinw et EtOH. [15] In 2015, Li et al disclosed ar adical5 -exo-dig cyclization of phenol-linked 1,6-enynes using molecular oxygen, TEMPO, and TBN under am etal-free condition. In this reaction, TBN helps in the oxidative cleavage of the NÀOb ond of TEMPO.…”

Section: Oxidationmentioning

confidence: 99%

tert‐Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

Dahiya

Sahoo

Alam

et al. 2019

Chemistry An Asian Journal

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The upsurge interesti nt he development of efficient methodologies for the constructiono fn itrogen-containing frameworks via the use of expedient reagents have been creating ar enaissance in contemporary organic chemistry.I nt his perspective, tertbutyl nitrite (TBN) is an emerging building block. Due to its uniques tructuralf eatures, it shows differential reactivity under different reaction conditions. These diverse reactivities have resulted in the construction of ad iverse array of complex N-containing molecules. The primary objective of the presentr eview is to bring the latest findings of TBN in terms of its applications in reactions (oxidation, diazotization, nitrosation, nitration, oximation, N-synthon, and miscellaneous reactions) into the limelight.F or simplicity and brevity,r eactions in each section are explained with the mechanism of formation and selected examples are given.Scheme1.Differential reactivity of TBN. 4455 MinireviewScheme4.Visible-light-promoted synthesis of selenide ethers.Scheme5.Proposed mechanism for visible-light-promoted synthesis of selenide ethers.Scheme6.TBN-mediated synthesis of selenide ethers.Scheme7.Metal-free synthesis of 4-carbonylquinolines.Scheme8.Proposed mechanism for synthesis of 4-carbonylquinolines.Scheme9.TBN-mediated demethylative borylation of methylarenes.Scheme10. Plausible mechanism for demethylative borylation of methylarenes.Scheme11. Trifluoromethylation of various aromatic amine substrates.Scheme12. Copper-catalyzed isoperfluoropropylation of anilines.Scheme13. Plausible mechanism for Cu-catalyzed isoperfluoropropylation of anilines.Scheme14. TBN-mediateddiazotizative allylation of aromatic amines.Scheme15. Oxidativecyanomethylationo fa lkenes via CÀHb ond activation.Scheme16. TBN-mediatedand Cu-catalyzedsynthesis of thioether.

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“…The Wacker oxidation usually gives ketones as reaction products, but the literature reports that one can carry out the Wacker process that will give 99% selectivity in obtaining aldehydes, e.g., using 1,4-benzoquinone, t-BuOH, and PdCl 2 (MeCN) 2 [ 15 , 16 , 17 , 18 ]. Regarding the selectivity of the Wacker process, products with high selectivity are also obtained using styrene derivatives as substrates with the reaction carried out under mild conditions [ 19 ].…”

Section: Oxidation Processesmentioning

confidence: 99%

Application of Coordination Compounds with Transition Metal Ions in the Chemical Industry—A Review

Malinowski

Zych

Jacewicz

et al. 2020

IJMS

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This publication presents the new trends and opportunities for further development of coordination compounds used in the chemical industry. The review describes the influence of various physicochemical factors regarding the coordination relationship (for example, steric hindrance, electron density, complex geometry, ligand), which condition technological processes. Coordination compounds are catalysts in technological processes used during organic synthesis, for example: Oxidation reactions, hydroformylation process, hydrogenation reaction, hydrocyanation process. In this article, we pointed out the possibilities of using complex compounds in catalysis, and we noticed what further research should be undertaken for this purpose.

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Tuning Regioselectivity of Wacker Oxidation in One Catalytic System: Small Change Makes Big Step

Cited by 37 publications

References 45 publications

Micellar Catalysis for Sustainable Hydroformylation

Micellar Catalysis for Sustainable Hydroformylation

tert‐Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

Application of Coordination Compounds with Transition Metal Ions in the Chemical Industry—A Review

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