- N -Heterocyclic carbene (NHC) catalyzed amidation of aldehydes with amines via the tandem N -hydroxysuccinimide ester formation
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A facile method for the amidation of aldehydes by a cascade approach was developed. This methodology, reported for the first time, uses a N-heterocyclic carbene (NHC) as the catalyst, and N-hydroxysuccinimide (NHS) mediated synthesis of amides utilising TBHP as the oxidant. Various substituted aldehydes reacted smoothly with NHS giving the corresponding active esters in moderate to good yields, which facilely converted into amides in one pot. In addition, the drug moclobemide was synthesized to represent the practical utility of the developed methodology. This journal is
- Singh, Ashmita,Narula
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supporting information
p. 7486 - 7490
(2021/05/13)
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- A photoinduced cross-dehydrogenative-coupling (CDC) reaction between aldehydes and N-hydroxyimides by a TiO2-Co ascorbic acid nanohybrid under visible light irradiation
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In this study, we performed a visible light-mediated aerobic photo-cross dehydrogenative coupling (CDC) reaction between aldehydes and N-hydroxyimides using TiO2-AA-Co as a photocatalyst for the synthesis of active esters. The synergistic and selective effects of the cobalt ascorbic acid complex (Co-AA) and TiO2 nanoparticles on the visible-light photocatalytic activity were explored. The method possesses some advantages such as environmentally friendly conditions, easy work-up procedure, reusability, and scalability.
- Feizpour, Fahimeh,Jafarpour, Maasoumeh,Rezaeifard, Abdolreza
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supporting information
p. 807 - 811
(2018/02/06)
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- Iron-Nitrate-Catalyzed Oxidative Esterification of Aldehydes and Alcohols with N-Hydroxyphthalimide: Efficient Synthesis of N-Hydroxyimide Esters
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An Fe(NO3)3·9H2O-catalyzed cross-dehydrogenative coupling reaction between N-hydroxyphthalimide (NHPI) or N-hydroxysuccinimide (NHSI) and aldehydes or alcohols in air is described. This transformation represents an efficient approach to the preparation of N-hydroxyimide ester derivatives in moderate to excellent yields, and has a wide substrate scope.
- Xu, Xiaohe,Sun, Jian,Lin, Yuyan,Cheng, Jingya,Li, Pingping,Jiang, Xiaoying,Bai, Renren,Xie, Yuanyuan
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supporting information
p. 7160 - 7166
(2017/12/28)
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- Cross dehydrogenative coupling (CDC) of aldehydes with N-hydroxyimides by visible light photoredox catalysis
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A photoinduced cross-dehydrogenative-coupling (CDC) reaction between aldehydes and N-hydroxyimides has been developed for the synthesis of ester derivatives. Using 2 mol% [Ru(bpy)3]Cl2 in dry acetonitrile at room temperature with an LED light bulb, we were able to synthesize N-hydroxyesters in good yields. The ester derivatives are very useful synthetic intermediates, which were transformed to amide and oxazole building blocks in excellent yields. This journal is
- Dinda, Milan,Bose, Chandan,Ghosh, Tridev,Maity, Soumitra
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p. 44928 - 44932
(2015/06/02)
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- Palladium-Catalyzed Carbonylation of (Hetero)Aryl, Alkenyl and Allyl Halides by Means of N-Hydroxysuccinimidyl Formate as CO Surrogate
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An efficient Pd-catalyzed carbonylation protocol is described for the coupling of a large panel of aryl, heteroaryl, benzyl, vinyl and allyl halides 2 with the unusual N-hydroxysuccinimidyl (NHS) formate 1 as a CO surrogate to afford the corresponding valuable NHS esters 3. High conversion to the coupling products was achieved with up to 98% yield by means of Pd(OAc)2/Xantphos catalyst system.
- Barré, Ana?s,T?nta?, Mihaela-Liliana,Alix, Florent,Gembus, Vincent,Papamica?l, Cyril,Levacher, Vincent
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p. 6537 - 6544
(2015/10/05)
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- One-pot synthesis of hydroxamic acids from aldehydes and hydroxylamine
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A one-pot oxidative transformation of aldehydes into hydroxamic acids by the use of an aqueous solution of hydroxylamine is reported. The methodology gives high yields and makes use of cheap, abundant and easily available reagents.
- Dettori, Giovanna,Gaspa, Silvia,Porcheddu, Andrea,De Luca, Lidia
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supporting information
p. 2709 - 2713
(2014/09/17)
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- Scalable synthesis of N -acylaziridines from N -tosylaziridines
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N-Acylaziridines are important starting materials for the synthesis of chiral amine derivatives. The traditional methods for producing these activated aziridines have significant drawbacks. The gram scale synthesis of N-acylaziridines by deprotection of N
- Rubin, Heather,Cockrell, Jennifer,Morgan, Jeremy B.
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p. 8865 - 8871
(2013/09/24)
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- A copper-catalysed amidation of aldehydes via N-hydroxysuccinimide ester formation
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A copper-catalysed oxidative amidation of aldehydes via N-hydroxysuccinimide ester formation is reported. The methodology employed to prepare amides directly from aldehydes has a very wide scope, is high yielding, and does not need dry conditions. This cross-coupling reaction appears to be simple and makes use of cheap, abundant and easily available reagents.
- Pilo, Monica,Porcheddu, Andrea,De Luca, Lidia
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p. 8241 - 8246
(2013/12/04)
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- Metal-free oxidative amide formation with N-hydroxysuccinimide and hypervalent iodine reagents
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An oxidative amide formation using N-hydroxysuccinimide and hypervalent iodine reagents was developed. The method enables a wide range of aldehydes and amines to be coupled under mild reaction conditions providing amide in good to excellent yield. The radical species in the reaction mixture was observed for the first time using ESR measurement, and along with other mechanistic investigations, a plausible mechanism of the reaction was proposed.
- Yao, Haoyi,Tang, Yun,Yamamoto, Kana
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supporting information; experimental part
p. 5094 - 5098
(2012/10/08)
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- Aerobic amide bond formation with N-hydroxysuccinimide
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Breathe easy: Molecular oxygen is one of the most abundant, atom-efficient, and economical oxidants. An aerobic oxidative amide formation from aldehydes and amines is reported. The method uses a catalytic amount of Co(OAc) 2 and N-hydroxysuccinimide as reaction promoters. It is applicable to chiral substrates without loss of their optical purity. Copyright
- Yao, Haoyi,Yamamoto, Kana
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supporting information; experimental part
p. 1542 - 1545
(2012/09/08)
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- Convenient synthesis of N-hydroxysuccinimide esters from carboxylic acids using triphosgene
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A simple and convenient method for the synthesis of N-hydroxysuccinimide ester is developed using triphosgene as an acid activator. Several aromatic and aliphatic N-hydroxysuccinimide esters are prepared from their corresponding carboxylic acids at room temperature in good yields in a rapid process using triphosgene. Some of the major advantages are mild conditions, good yields, and easy operation.
- Kim, Misoo,Han, Ki-Jong
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experimental part
p. 4467 - 4472
(2010/05/01)
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- N-hydroxysuccinimide-promoted oxidation of primary alcohols and aldehydes to form active esters with hypervalent(III) iodine
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A simple, mild, and efficient method for the conversion of primary alcohols and aldehydes to N-hydroxysuccinimide esters with (diacetoxyiodo)benzene in high yield is developed. N-Hydroxysuccinimide acts not only as an esterification partner but also as an activator of PhI(OAc)2 in this reaction. Copyright
- Wang, Naiwei,Liu, Renhua,Xu, Qing,Liang, Xinmiao
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p. 566 - 567
(2007/10/03)
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- IBX-mediated conversion of primary alcohols and aldehydes to N-hydroxysuccinimide esters
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Recently, the use of the hypervalent iodine reagent 1-hydroxy-1,2- benziodoxol-3(1H)-one 1-oxide (IBX) for the oxidation of primary alcohols and aldehydes to carboxylic acids was described. During the synthesis of these carboxylic acids the corresponding N-hydroxysuccinimide esters were formed as intermediate products, but their isolation as main reaction products was not successful. We report herein a simple and very efficient method to prepare these synthetically valuable active esters.
- Schulze, Agnes,Giannis, Athanassios
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p. 252 - 256
(2007/10/03)
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- PROCESS FOR CONVERSION OF PHENOLS TO CARBOXAMIDES VIA THE SUCCINIMIDE ESTERS
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A process for converting an aryl triflate, heteroaryl triflate, aryl halide or heteroaryl halide to an N-hydroxysuccinimido este is disclosed. The process involves reacting the triflate or halide with carbon monoxide and N-hydroxysuccinimide in a solvent in the presence of a palladium catalyst and a base.
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- Preparation of N-hydroxysuccinimido esters via palladium-catalyzed carbonylation of aryl triflates and halides
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N-Hydroxysuccinimido esters of aromatic carboxylic acids (a.k.a. active esters) can be made using a potentially general, one-step procedure via Pd-catalyzed carbonylation of an aryl triflate or aryl iodide with CO and N-hydroxysuccinimide. Excellent yields (up to 94%) were observed when the reaction was done in DMSO at 70°C and 1 atmosphere of CO pressure.
- Lou, Rongliang,VanAlstine, Melissa,Sun, Xufeng,Wentland, Mark P.
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p. 2477 - 2480
(2007/10/03)
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- Radiosensitizing nitrobenzoic acid amide derivatives
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Nitrobenzoic acid amide derivative represented by the formula STR1 wherein A is (CH2)x NH(CH2)y or (CH2)x NH(CH2)y NH(CH2)z, n is 1 or 2, x, y an
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