Pyridyl‐(2)‐Glykolsäure

Sauermilch, Walter

doi:10.1002/cber.19570900531

Cited by 9 publications

(3 citation statements)

References 2 publications

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“…The crude product was chromatographed on silica (petroleum ether/EtOAc) to give a white solid, mp 154–156 °C [156 °C], 44% (28.5 mg). dl- 7g : 1 H NMR (400 MHz, CDCl 3 ) δ 8.44 (d, J = 4.8 Hz, 2H), 7.66 (t, J = 7.7 Hz, 2H), 7.50 (s, 2H), 7.18–7.14 (m, 2H), 5.17 (s, 2H).…”

Section: Methodsmentioning

confidence: 99%

Visible Light Induced Reduction and Pinacol Coupling of Aldehydes and Ketones Catalyzed by Core/Shell Quantum Dots

Yang

Wang

et al. 2021

J. Org. Chem.

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We present an efficient and versatile visible light-driven methodology to transform aryl aldehydes and ketones chemoselectively either to alcohols or to pinacol products with CdSe/CdS core/shell quantum dots as photocatalysts. Thiophenols were used as proton and hydrogen atom donors and as hole traps for the excited quantum dots (QDs) in these reactions. The two products can be switched from one to the other simply by changing the amount of thiophenol in the reaction system. The core/shell QD catalysts are highly efficient with a turn over number (TON) larger than 4 × 104 and 4 × 105 for the reduction to alcohol and pinacol formation, respectively, and are very stable so that they can be recycled for at least 10 times in the reactions without significant loss of catalytic activity. The additional advantages of this method include good functional group tolerance, mild reaction conditions, the allowance of selectively reducing aldehydes in the presence of ketones, and easiness for large scale reactions. Reaction mechanisms were studied by quenching experiments and a radical capture experiment, and the reasons for the switchover of the reaction pathways upon the change of reaction conditions are provided.

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Section: Methodsmentioning

confidence: 99%

Visible Light Induced Reduction and Pinacol Coupling of Aldehydes and Ketones Catalyzed by Core/Shell Quantum Dots

Yang

Wang

et al. 2021

J. Org. Chem.

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“…This work is dedicated to development of new scalable synthetic pathways to pyridinyl and piperidinyl substituted ethane-1,2-diols and oxiranes, namely: 1-(pyridin-2-yl)ethane-1,2-diol, [1] 2-(oxiran-2-yl)pyridine [2] and two diastereomeric forms of 1-(piperidin-2-yl)ethane-1,2-diol. [3] Although, these compounds are well-known, they have never been regarded as promising starting materials for the synthesis of novel chiral macrocyclic compounds, the properties of which can be varied in a wide range, depending on configuration of their stereogenic centres and a degree of stereoregularity in decoration of the cyclic polyether core with incorporative fragments of nitrogen heterocycles.…”

Section: Introductionmentioning

confidence: 99%

“…This prompted us to develop new procedures for their preparation, which are capable to satisfy the demands of the ongoing template synthesis of macrocycles, based on using these scaffolds. [1] Experimental IR spectra were recorded on a Specord M-82 spectrometer in Nujol mulls, and wave numbers, ν, were expressed in cm -1 . 1 H and 13 C NMR spectra were recorded on a AV Bruker (600 MHz) spectrometer, and shifts, δ, are given in ppm downfield from TMS as an internal standard.…”

Section: Introductionmentioning

confidence: 99%