Synthesis, X-Ray Crystallography, and Reactions of <i>N</i>-Acyl and <i>N</i>-Carbamoyl Succinimides

Goodman, Cassie A.; Eagles, Joel B.; Rudahindwa, Leandre; Hamaker, Christopher G.; Hitchcock, Shawn R.

doi:10.1080/00397911.2012.690061

Cited by 15 publications

(8 citation statements)

References 14 publications

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“…These imides are highly stable and easily accessed from the corresponding carboxylic acids. 16 The proposed mechanism for this transformation, which is adapted from our studies on the cross-coupling of aryl halides with alkyltrifluoroborates, is shown in Scheme 3 . 17 …”

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confidence: 99%

Synergistic Visible-Light Photoredox/Nickel-Catalyzed Synthesis of Aliphatic Ketones via N–C Cleavage of Imides

et al. 2017

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An electrophilic, imide-based, visible-light-promoted photoredox/Ni-catalyzed cross-coupling reaction for the synthesis of aliphatic ketones has been developed. This protocol proceeds through N–C(O) bond activation, made possible through the lower activation energy for metal insertion into this bond due to delocalization of the lone pair of electrons on the nitrogen by electron-withdrawing groups. The operationally simple and mild cross-coupling reaction is performed at ambient temperature and exhibits tolerance for a variety of functional groups.

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confidence: 99%

Synergistic Visible-Light Photoredox/Nickel-Catalyzed Synthesis of Aliphatic Ketones via N–C Cleavage of Imides

et al. 2017

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“…The N -BOC- N -methyl-acetamide 31 was prepared in a previous step from 25 by (BOC) 2 O reagent [ 82 , 83 ], a process known as N -Boc activation. Other, bisacyl and triacyl substituted amides (such as succinimide [ 84 ] and phthalimide derivatives [ 85 ]) may also behave as good transamidating agents in the presence of an amine. In all cases, the listed ΔAM values were large enough to provide enough driving force to convert to the desired product 26 [ 40 ].…”

Section: Discussionmentioning

confidence: 99%

Amide Activation in Ground and Excited States

et al. 2018

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Not all amide bonds are created equally. The purpose of the present paper is the reinterpretation of the amide group by means of two concepts: amidicity and carbonylicity. These concepts are meant to provide a new viewpoint in defining the stability and reactivity of amides. With the help of simple quantum-chemical calculations, practicing chemists can easily predict the outcome of a desired process. The main benefit of the concepts is their simplicity. They provide intuitive, but quasi-thermodynamic data, making them a practical rule of thumb for routine use. In the current paper we demonstrate the performance of our methods to describe the chemical character of an amide bond strength and the way of its activation methods. Examples include transamidation, acyl transfer and amide reductions. Also, the method is highly capable for simple interpretation of mechanisms for biological processes, such as protein splicing and drug mechanisms. Finally, we demonstrate how these methods can provide information about photo-activation of amides, through the examples of two caged neurotransmitter derivatives.

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“…An appropriate N ‐acylsuccinimide ( 1 ; 0.5 mmol), synthesized according to a previously reported procedure, and 0.6 mmol of phenylboronic acid 2 were added to a 10 ml round‐bottom flask fitted with a magnetic stirrer containing a suspension of catalyst (0.03 mol%) in 2 ml of DES (choline chloride–glycerol, 1:2). The resultant mixture was vigorously stirred at 90°C for 5 h. The progress of the reaction was monitored by TLC (ethyl acetate– n ‐hexane).…”

Section: Methodsmentioning

confidence: 99%

Novel palladium nanoparticles supported on β‐cyclodextrin@graphene oxide as magnetically recyclable catalyst for Suzuki–Miyaura cross‐coupling reaction with two different approaches in bio‐based solvents

Heidari

Heravi

Nabid

et al. 2018

Applied Organom Chemis

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A novel nanocatalyst was designed and prepared. Initially, the surface of magnetic graphene oxide (M-GO) was modified using thionyl chloride, tris(hydroxymethyl)aminomethane and acryloyl chloride as linkers which provide reactive C═C bonds for the polymerization of vinylic monomers. Separately, β-cyclodextrin (β-CD) was treated with acryloyl chloride to provide a modified β-CD. Then, in the presence methylenebisacrylamide as a crosslinker, monomers of modified β-CD and acrylamide were polymerized on the surface of the pre-prepared M-GO. Finally, palladium acetate and sodium borohydride were added to this composite to afford supported palladium nanoparticles. This fabricated nanocomposite was fully characterized using various techniques. The efficiency of this easily separable and reusable heterogeneous catalyst was successfully examined in Suzuki-Miyaura cross-coupling reactions of aryl halides and boronic acid as well as in modified Suzuki-Miyaura crosscoupling reactions of N-acylsuccinimides and boronic acid in green media. The results showed that the nanocatalyst was efficient in coupling reactions for direct formation of the corresponding biphenyl as well as benzophenone derivatives in green media based on bio-based solvents. In addition, the nanocatalyst was easily separable, using an external magnet, and could be reused several times without significant loss of activity under the optimum reaction conditions.

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Synthesis, X-Ray Crystallography, and Reactions of N-Acyl and N-Carbamoyl Succinimides

Cited by 15 publications

References 14 publications

Synergistic Visible-Light Photoredox/Nickel-Catalyzed Synthesis of Aliphatic Ketones via N–C Cleavage of Imides

Synergistic Visible-Light Photoredox/Nickel-Catalyzed Synthesis of Aliphatic Ketones via N–C Cleavage of Imides

Amide Activation in Ground and Excited States

Novel palladium nanoparticles supported on β‐cyclodextrin@graphene oxide as magnetically recyclable catalyst for Suzuki–Miyaura cross‐coupling reaction with two different approaches in bio‐based solvents

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