One-pot C–C/C–O bond formation: synthesis of spirocyclic lactones

RSC Advances ◽  
2016 ◽  
Vol 6 (2) ◽  
pp. 837-843 ◽  
Author(s):  
Pedireddi Niharika ◽  
Gedu Satyanarayana

An efficient and practical method for the synthesis of novel spiro(tri or tetra)cyclic lactones via the formation of C–C and C–O bonds in one-pot is presented.

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

2018 ◽  
Vol 90 (4) ◽  
pp. 607-616
Author(s):  
Yin-Ping Wang ◽  
Yue-Jian Lin ◽  
Guo-Xin Jin

AbstractFor the first time, carborane complexes containing a B(4)–S bond were obtained directly by heating mononuclear Pd-B(4)-bound carborane complexes. A possible mechanism involved in sulfur atom migration is presented in which the leaving group, pyridine, benzyl isocyanide or PPh3, is demonstrated to be the trigger of the reaction process. In this work, efficient routes are developed through one-pot reactions to prepare B(4)-S carborane derivatives.


CCS Chemistry ◽  
2020 ◽  
pp. 2764-2771
Author(s):  
Bao-Gui Cai ◽  
Shuai-Shuai Luo ◽  
Lin Li ◽  
Lei Li ◽  
Jun Xuan ◽  
...  

Synthesis ◽  
2010 ◽  
Vol 2010 (15) ◽  
pp. 2577-2582 ◽  
Author(s):  
Hong Liu ◽  
Haifeng Sun ◽  
Deju Ye ◽  
Hualiang Jiang ◽  
Kaixian Chen

ChemInform ◽  
2015 ◽  
Vol 46 (13) ◽  
pp. no-no
Author(s):  
Trimurtulu Kotipalli ◽  
Donala Janreddy ◽  
Veerababurao Kavala ◽  
Chun-Wei Kuo ◽  
Ting-Shen Kuo ◽  
...  

Synthesis ◽  
2020 ◽  
Vol 52 (07) ◽  
pp. 1035-1046 ◽  
Author(s):  
Meng-Yang Chang ◽  
Shin-Mei Chen ◽  
Yu-Ting Hsiao

Trifluoroacetic anhydride mediated one-pot intermolecular formal (4+2) benzannulation of oxygenated arylacetic acids with alkyl aryl ketones provides 4-aryl-2-arylacetoxynaphthalenes in moderate to good yields in the presence of H3PO4 in an open-vessel in a straightforward procedure. A plausible mechanism is proposed and discussed. This protocol provides a highly effective ring-closure via two carbon–carbon (C–C) and one carbon–oxygen (C–O) bond-formation events.


2019 ◽  
Vol 72 (12) ◽  
pp. 978 ◽  
Author(s):  
Dafne Saporito ◽  
Sergio A. Rodriguez ◽  
Maria T. Baumgartner

An eco-friendly and direct arylation of hydroxyaryls in water using photoinduced reactions with different substrates (1-bromo-2-naphthol, 1-iodo-2-naphthol, N-(2-iodophenyl)acetamide, 5-bromouracil, 2-iodo-N-methylbenzamide, and 2-iodobenzamide) was studied. For example, π-expanded coumarins, compounds with potential optical applications, were synthesized in very high yield, without the use of toxic reagents, in a one-pot reaction. In addition, we demonstrate that the irradiation source (halogen lamp) can be efficiently replaced by an LED without altering the reaction yield.


Synlett ◽  
2018 ◽  
Vol 29 (05) ◽  
pp. 548-555 ◽  
Author(s):  
Liang-Nian He ◽  
Xiao-Fang Liu ◽  
Xiao-Ya Li ◽  
Chang Qiao

Reductive functionalization of CO2 with amines and a reductant, which combines both reduction of CO2 and C–N bond formation in one pot to produce versatile chemicals and energy-storage materials such as formamides, aminals, and methylamines that are usually derived from petroleum feedstock, would be appealing and promising. Herein, we give a brief review on recent developments in the titled CO2 chemistry by employing transition-metal-free catalysis, which can be catalogued as below according to the diversified energy content of the products, that is formamides, aminals, and methylamines being consistent with 2-, 4-, and 6-electron reduction of CO2, respectively. Notably, hierarchical reduction of CO2 with amines to afford at least two products, for example, formamides and methylamines, could be realized with the same catalyst through tuning the hydrosilane type, reaction temperature, or CO2 pressure. Finally, the opportunities and challenges of the reductive functionalization of CO2 with amines are also highlighted.1 Introduction2 2-Electron Reduction of CO2 to Formamide3 6-Electron Reduction of CO2 to Methylamine4 4-Electron Reduction of CO2 to Aminal5 Hierarchical Reduction of CO2 with Amines6 Conclusion


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