Vanadium-Catalyzed Oxidative C(CO)–C(CO) Bond Cleavage for C–N Bond Formation: One-Pot Domino Transformation of 1,2-Diketones and Amidines into Imides and Amides

2017 ◽  
Vol 82 (14) ◽  
pp. 7332-7345 ◽  
Author(s):  
Chander Singh Digwal ◽  
Upasana Yadav ◽  
P. V. Sri Ramya ◽  
Sravani Sana ◽  
Baijayantimala Swain ◽  
...  
Keyword(s):  
Molecules ◽  
2019 ◽  
Vol 24 (9) ◽  
pp. 1671 ◽  
Author(s):  
Xiu Wang ◽  
Zhenhua Wang ◽  
Li Liu ◽  
Yuya Asanuma ◽  
Yasushi Nishihara

Nickel-catalyzed decarbonylative stannylation of acyl fluorides under ligand-free conditions was disclosed. A variety of aromatic acyl fluorides are capable of reacting with silylstannanes in the presence of cesium fluoride. A one-pot decarbonylative stannylation/Migita-Kosugi-Stille reaction of benzoyl fluoride, giving rise to the direct formation of the corresponding cross-coupled products, further demonstrated the synthetic utility of the present method. This newly developed methodology with a good functional-group compatibility via C–F bond cleavage and C–Sn bond formation under nickel catalysis opens a new area for the functionalization of acyl fluorides in terms of carbon-heteroatom bond formation.


2015 ◽  
Vol 51 (73) ◽  
pp. 13976-13979 ◽  
Author(s):  
Isai Ramakrishna ◽  
Gowri Sankar Grandhi ◽  
Harekrishna Sahoo ◽  
Mahiuddin Baidya

A practical protocol for the α-amination of ketones (up to 99% yield) has been developed via the Mukaiyama aldol reaction of in situ generated nitrosocarbonyl compounds.


2015 ◽  
Vol 13 (29) ◽  
pp. 7973-7978 ◽  
Author(s):  
Vunnam Venkateswarlu ◽  
K. A. Aravinda Kumar ◽  
Sorav Gupta ◽  
Deepika Singh ◽  
Ram A. Vishwakarma ◽  
...  

One-pot I2/DMSO mediated metal-free C–C bond cleavage of aryl-/heteroaryl- or aliphatic α-ketoaldehydes offering a carboxylic acid followed by esterification is presented.


RSC Advances ◽  
2016 ◽  
Vol 6 (104) ◽  
pp. 102023-102027 ◽  
Author(s):  
Xiuling Chen ◽  
Yan Li ◽  
Minghu Wu ◽  
Haibing Guo ◽  
Longqiang Jiang ◽  
...  

A novel protocol to synthesize tert-butyl esters from benzyl cyanides and tert-butyl hydroperoxide has been successfully achieved. Csp3–H bond oxidation, C–CN bond cleavage and C–O bond formation proceeded smoothly in one pot under the metal-free condition.


ChemInform ◽  
2015 ◽  
Vol 46 (46) ◽  
pp. no-no
Author(s):  
Vunnam Venkateswarlu ◽  
K. A. Aravinda Kumar ◽  
Sorav Gupta ◽  
Deepika Singh ◽  
Ram A. Vishwakarma ◽  
...  

2018 ◽  
Vol 5 (15) ◽  
pp. 2317-2321 ◽  
Author(s):  
Jiao-xia Zou ◽  
Yong-qiang Wang ◽  
Long-tao Huang ◽  
Yi Jiang ◽  
Jin-hong Chen ◽  
...  

A new and practical approach to α-dithioacetal/α-diselenoacetal amides has been developed.


2020 ◽  
Author(s):  
Lucas A. Freeman ◽  
Akachukwu D. Obi ◽  
Haleigh R. Machost ◽  
Andrew Molino ◽  
Asa W. Nichols ◽  
...  

The reduction of the relatively inert carbon–oxygen bonds of CO<sub>2</sub> to access useful CO<sub>2</sub>-derived organic products is one of the most important fundamental challenges in synthetic chemistry. Facilitating this bond-cleavage using earth-abundant, non-toxic main group elements (MGEs) is especially arduous because of the difficulty in achieving strong inner-sphere interactions between CO<sub>2</sub> and the MGE. Herein we report the first successful chemical reduction of CO<sub>2</sub> at room temperature by alkali metals, promoted by a cyclic(alkyl)(amino) carbene (CAAC). One-electron reduction of CAAC-CO<sub>2</sub> adduct (<b>1</b>) with lithium, sodium or potassium metal yields stable monoanionic radicals clusters [M(CAAC–CO<sub>2</sub>)]<sub>n</sub>(M = Li, Na, K, <b> 2</b>-<b>4</b>) and two-electron alkali metal reduction affords open-shell, dianionic clusters of the general formula [M<sub>2</sub>(CAAC–CO<sub>2</sub>)]<sub>n </sub>(<b>5</b>-<b>8</b>). It is notable that these crystalline clusters of reduced CO<sub>2</sub> may also be isolated via the “one-pot” reaction of free CO<sub>2</sub> with free CAAC followed by the addition of alkali metals – a reductive process which does not occur in the absence of carbene. Each of the products <b>2</b>-<b>8</b> were investigated using a combination of experimental and theoretical methods.<br>


2020 ◽  
Vol 7 (1) ◽  
pp. 23-39 ◽  
Author(s):  
Kantharaju Kamanna ◽  
Santosh Y. Khatavi

Multi-Component Reactions (MCRs) have emerged as an excellent tool in organic chemistry for the synthesis of various bioactive molecules. Among these, one-pot MCRs are included, in which organic reactants react with domino in a single-step process. This has become an alternative platform for the organic chemists, because of their simple operation, less purification methods, no side product and faster reaction time. One of the important applications of the MCRs can be drawn in carbon- carbon (C-C) and carbon-heteroatom (C-X; X = N, O, S) bond formation, which is extensively used by the organic chemists to generate bioactive or useful material synthesis. Some of the key carbon- carbon bond forming reactions are Grignard, Wittig, Enolate alkylation, Aldol, Claisen condensation, Michael and more organic reactions. Alternatively, carbon-heteroatoms containing C-N, C-O, and C-S bond are also found more important and present in various heterocyclic compounds, which are of biological, pharmaceutical, and material interest. Thus, there is a clear scope for the discovery and development of cleaner reaction, faster reaction rate, atom economy and efficient one-pot synthesis for sustainable production of diverse and structurally complex organic molecules. Reactions that required hours to run completely in a conventional method can now be carried out within minutes. Thus, the application of microwave (MW) radiation in organic synthesis has become more promising considerable amount in resource-friendly and eco-friendly processes. The technique of microwaveassisted organic synthesis (MAOS) has successfully been employed in various material syntheses, such as transition metal-catalyzed cross-coupling, dipolar cycloaddition reaction, biomolecule synthesis, polymer formation, and the nanoparticle synthesis. The application of the microwave-technique in carbon-carbon and carbon-heteroatom bond formations via MCRs with major reported literature examples are discussed in this review.


2017 ◽  
Vol 28 (6) ◽  
pp. e21408 ◽  
Author(s):  
Samia Guezane-Lakoud ◽  
Martial Toffano ◽  
Louisa Aribi-Zouioueche

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