Atmospheric oxidative catalyst-free cross-dehydrogenative coupling of aldehydes with N -hydroxyimides

Xu, Xiaohe; Li, Pingping; Huang, Yingyi; Tong, Chuo; Yan, Yiyan; Xie, Yuanyuan

doi:10.1016/j.tetlet.2017.03.064

Cited by 27 publications

(6 citation statements)

References 31 publications

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“…13 C{ 1 H} NMR (CDCl 3 , 101 MHz) δ 169.1 (2C), 162.5 (d, 1C, J = 263.2 Hz), 159.3, 136.8 (d, 1C, J = 9.3 Hz), 132.6, 124.5, 117.4 (d, 1C J = 21.9 Hz), 113.8 (d, 1C, J = 9.3 Hz), 25.6 (2C). These data are in agreement with those previously reported …”

Section: Methodssupporting

confidence: 94%

Formation of 1-Hydroxymethylene-1,1-bisphosphinates through the Addition of a Silylated Phosphonite on Various Trivalent Derivatives

et al. 2020

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An easily handled one-pot synthetic procedure was previously developed for the synthesis of bisphosphinates starting from acyl chlorides. Herein, other trivalent derivatives as acid anhydrides and activated esters were tested to form various bisphosphinates. This modulation of the reactivity can be controlled according to the nature of the acid derivative for the use of sensitive and functionalized substrates.

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Section: Methodssupporting

confidence: 94%

Formation of 1-Hydroxymethylene-1,1-bisphosphinates through the Addition of a Silylated Phosphonite on Various Trivalent Derivatives

et al. 2020

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“…Sterically encumbered NHPI esters can be prepared by reacting corresponding acid chlorides with the potassium salt of N -hydroxyphthalimide in the presence of a suitable crown ether . Additionally, NHPI esters can also be accessed through cross-dehydrogenative coupling (CDC) of aldehydes and N -hydroxyphthalimides . In 1988, Okada, Oda, and co-workers revealed that alkyl radicals could be generated from the corresponding NHPI esters through photosensitization or under photoredox catalysis .…”

Section: Introductionmentioning

confidence: 99%

Single Electron Transfer-Induced Redox Processes Involving N-(Acyloxy)phthalimides

et al. 2021

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The past decade has witnessed the emergence of N-(acyloxy)phthalimides (NHPI esters) and its derivatives at the forefront of synthetic methods facilitating the construction of diverse molecular frameworks from the readily available carboxylic acid feedstock. The NHPI esters are predisposed to undergo reductive fragmentation via a single electron transfer (SET) process under thermal, photochemical, or electrochemical conditions to generate the corresponding carbon-or nitrogencentered radicals that participate in a multitude of synthetic transformations to forge carbon−carbon and carbon−heteroatom bonds. The chemistry involving NHPI esters has received broad applicability not only in well-designed cascade annulations but also in medicinal chemistry and natural product synthesis. This comprehensive Review, broadly categorized according to the nature of the bond formation, details the progress made in this field since the initial discovery by providing representative examples with mechanistic details, with an emphasis on challenges and future directions.

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“…Imide- N -oxyl radicals proved to be useful H-atom abstracting agents due to the high activity, mild conditions of generation, and slow self-decay − compared with other O-centered radicals. Thus, precursors of such radicals, N -hydroxyimides (NHI), were successfully used as OH-reagents in cross-dehydrogenative C–O coupling with substrates containing benzyl, − allyl, , aldehyde, − ether , moieties, and even with cycloalkanes. , Nevertheless, the imide- N -oxyl radical-based approach found scant application in the oxidative C–O coupling employing the nonaldehyde carbonyl compounds, presumably due to the inertness of C–H bonds in α-position to the carbonyl group. The scope of such reactions was limited to the highly CH-acidic β-dicarbonyl compounds (Scheme , A) and the aryl alkyl ketones having a primary alkyl substituent (Scheme , B). ,, …”

Section: Introductionmentioning

confidence: 99%

Metal-Free Cross-Dehydrogenative C–O Coupling of Carbonyl Compounds with N-Hydroxyimides: Unexpected Selective Behavior of Highly Reactive Free Radicals at an Elevated Temperature

et al. 2019

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Cross-dehydrogenative C−O coupling of N-hydroxyimides with ketones, esters, and carboxylic acids was achieved employing the di-tertbutyl peroxide as a source of free radicals and a dehydrogenating agent. The proposed method is experimentally simple and demonstrates the outstanding efficiency for the challenging CH substrates, such as unactivated esters and carboxylic acids. It was shown that N-hydroxyphthalimide drastically affects the oxidative properties of t-BuOOt-Bu by intercepting the t-BuO • radicals with the formation of phthalimide-N-oxyl radicals, a species responsible for both hydrogen atom abstraction from the CH reagent and the selective formation of the C−O coupling product by selective radical cross-recombination. The practical applicability of the developed method was exemplified by the single-stage synthesis of commercial reagent (known as Baran aminating reagent precursor) from isobutyric acid and N-hydroxysuccinimide, whereas in the standard synthetic approach, four stages are necessary.

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Atmospheric oxidative catalyst-free cross-dehydrogenative coupling of aldehydes with N -hydroxyimides

Cited by 27 publications

References 31 publications

Formation of 1-Hydroxymethylene-1,1-bisphosphinates through the Addition of a Silylated Phosphonite on Various Trivalent Derivatives

Formation of 1-Hydroxymethylene-1,1-bisphosphinates through the Addition of a Silylated Phosphonite on Various Trivalent Derivatives

Single Electron Transfer-Induced Redox Processes Involving N-(Acyloxy)phthalimides

Metal-Free Cross-Dehydrogenative C–O Coupling of Carbonyl Compounds with N-Hydroxyimides: Unexpected Selective Behavior of Highly Reactive Free Radicals at an Elevated Temperature

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