DDQ-mediated oxidation of sp3 C–H bond for the direct synthesis of vicinal tricarbonyl compounds

Wang, Zhenglin; An, Xing‐Lan; Ge, Li‐Shi; Jin, Jing-Hai; Luo, Xiaoyan; Deng, Wei‐Ping

doi:10.1016/j.tet.2014.04.021

Cited by 36 publications

(16 citation statements)

References 77 publications

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“…Interestingly, a new species was detected, which could be identified by NMR and ESI‐MS analysis as the TEMPO‐substrate adduct 4 , obtained by the α‐oxyamination of the β‐ketoenehydrazine 2 g and the free radical TEMPO. α‐Oxyamination between 1,3‐dicarbonyl compounds and TEMPO has been already reported . The formation of this adduct was almost undetectable when reacted compound 2 g and TEMPO in the absence of oxygen (entry 6).…”

Section: Resultsmentioning

confidence: 66%

Synthesis of α,β‐Dicarbonylhydrazones by Aerobic Manganese‐Catalysed Oxidation

et al. 2018

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A practical, simple, and efficient manganese-catalysed oxidation of C(sp 2 )ÀH bond in readily available b-carbonylenehydrazine under aerobic conditions has been developed. This protocol exhibits a wide range of functional group tolerance in b-carbonylenehydrazines to afford a,b-dicarbonylhydrazones. Experimental and theoretical results suggest that the reaction very likely proceeds through a radical pathway via a hydrogen-atom-transfer process promoted by a Mn III species.[ a] Reaction conditions: catalyst: Mn(OAc) 2 · 4H 2 O (0.0125 mmol), b-keto-enehydrazine (0.5 mmol), solvent: EtOH (10 mL), oxidant: O 2 (1 atm), t = 18 h, T = 60 8C. [b] Isolated yield. [c] Yield determined by NMR.

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Section: Resultsmentioning

confidence: 66%

Synthesis of α,β‐Dicarbonylhydrazones by Aerobic Manganese‐Catalysed Oxidation

et al. 2018

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“…The direct oxidation of β ‐keto amides 356 to 357 have also been achieved by DDQ/TEMPO, [160] Dess ‐ Martin periodinane (DMP), [161] Fe(NO 3 ) 3 /PhI=O [162] or PhI(COOCF 3 ) 2 (PIFA) [163] . Trivalent iodine compounds are versatile oxidants for the α ‐acyloxylation of β ‐keto amides to give 358 and 359 (Scheme 71).…”

Section: Reactivities Of β‐Keto Amidesmentioning

confidence: 99%

β‐Keto Amides: A Jack‐of‐All‐Trades Building Block in Organic Chemistry

Zheng

et al. 2021

Eur J Org Chem

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β‐Keto amides are a versatile class of compounds that find wide applications in organic chemistry owing to the juxtaposition of multiple reaction sites within their molecular structures. Due to the importance of β‐keto amides in modern organic chemistry, numerous novel preparation methods, synthetic applications and unprecedented reactivities have been recorded over the past decade. Taking advantage of transition‐metal‐catalysis and organocatalysis, β‐keto amides have emerged into a jack‐of‐all‐trades building block for many stereoselective or tandemized multicomponent reactions. But so far, no reviews have been documented on these recent achievements with β‐keto amides. Our Review aims to provide a thorough summary regarding: (a) the synthesis of β‐keto amides, (b) the reactivities of β‐keto amides, (c) the synthetic applications of β‐keto amides in various important heterocyclic compounds, and (d) the coordination of β‐keto amides with main group elements and transition metals and the relevant applications.

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“…Dynamic light scattering (DLS) is widely utilized to study the dynamics of soft matters. [51][52][53] The temporal intensity change of scattered light reflects the thermal fluctuation of the scattered objects. Calculating the autocorrelation function of the scattered light intensity can lead to the translational diffusion of the probe particles.…”

Section: Dynamic Light Scattering and Diffusing-ware Spectroscopymentioning

confidence: 99%

Rheological Study of Soft Matters: A Review of Microrheology and Microrheometers

Liu

2017

Macro Chemistry & Physics

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To overcome these shortcomings of macrorheology, a number of novel microrheological methods have emerged during the last few decades, [2] often involving a small tracking or probing particle (micrometer size) dispersed in a softmatter medium. By tracking the fluctuation due to thermal energy or applying an external force, usually in the form of magnetic force or optical trap, one can measure local mechanical responses. The local disturbance in a micrometer scale avoids reconstruction of local viscoelastic response, an inevitable problem in bulk rheology, especially when the probe particle size is smaller than the characteristic length of a soft matter. Depending on whether the probe is manipulated by an external force instead of a random walk due to thermal fluctuation, microrheometers can be generally characterized as active or passive ones. For an equilibrium system, the fluctuationdissipation theorem (FDT) guarantees that these two methods are equivalent. [3] In this review, we will detail these two classes of microrheometers, including their basic principles and typical setups as well as some recently developed hybrid microrheometers, [4][5][6] often used in characterizing polymer solutions and biological materials. Passive MicrorheologyIn a passive microrheometry method, the fluctuation of probes dispersed in a soft-matter medium is detected and analyzed by calculating the mean-square displacement (MSD) often from their video-based trajectories or scattered light intensities. Since the fluctuation of probes in space is driven by an extremely small thermal energy (k B T), the results from a passive method are always fallen inside the linear range of viscoelasticity. Generally, the elastic modulus is estimated within an upper limit of hundreds of Pa, which means that passive microrheometers are more suitable for measuring "soft" materials with a low viscosity and elasticity. Otherwise, the probes would be trapped without a measurable movement. Even newly developed super-resolution microscopes can provide a sub-nanometer resolution, [7] they are still not widely available methods and have a limited frequency range (up to 100 Hz). Mechanical properties of a soft matter can be obtained from MSD by using the generalized Stokes-Einstein relation (GSER). [8,9] In two extreme cases, (1) the probe is dispersed in a Newtonian viscous fluid and undergoes a Brownian motion with an MSD of 〈Δr 2 (t)〉. The viscosity η is related to the translational diffusion coefficient D as Microrheological TechniquesRheological properties of soft matter like polymer solutions/gels, colloidal dispersions, and biological materials have been extensively studied by macroscopic methods. Recently, a set of microrheometers has emerged as powerful tools to investigate the dynamics and structures of homogeneous or heterogeneous soft matter at the micro-or nanoscale. In this review, these microrheometers, including some novel hybrid microrheometers are summarized and compared.

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DDQ-mediated oxidation of sp3 C–H bond for the direct synthesis of vicinal tricarbonyl compounds

Cited by 36 publications

References 77 publications

Synthesis of α,β‐Dicarbonylhydrazones by Aerobic Manganese‐Catalysed Oxidation

Synthesis of α,β‐Dicarbonylhydrazones by Aerobic Manganese‐Catalysed Oxidation

β‐Keto Amides: A Jack‐of‐All‐Trades Building Block in Organic Chemistry

Rheological Study of Soft Matters: A Review of Microrheology and Microrheometers

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