ChemInform Abstract: N-Halosuccinimide/AgNO3-Efficient Reagent Systems for One-Step Synthesis of 2-Haloglycals from Glycals: Application in the Synthesis of 2C-Branched Sugars via Heck Coupling Reactions.

ChemInform ◽  
2014 ◽  
Vol 45 (32) ◽  
pp. no-no
Author(s):  
Suresh Dharuman ◽  
Yashwant D. Vankar
1999 ◽  
Vol 52 (2) ◽  
pp. 83 ◽  
Author(s):  
Christopher R. Strauss

Enabling technologies and methodologies were established and combined to afford various environmentally benign processes for laboratory-scale organic synthesis and for the production of fine chemicals, intermediates and pharmaceuticals. The technologies comprised continuous and batch microwave reactors and catalytic membranes. The methodologies included solvent-free conditions, catalysed or uncatalysed processes, the use of aqueous media at high temperature and non-extractive techniques for product isolation. Applications included Hofmann eliminations, Willgerodt and Jacobs–Gould reactions, indole transformations, aldol condensation, Rupe and Meyer–Schuster rearrangements and C–C coupling reactions (including a tandem Heck coupling–dehydrogenation). New processes for catalytic etherification, uncatalysed hydrogen transfer and a one-step arylamidation were also developed. Typical products were N-(4-hydroxyphenyl)acetamide, carvacrol, a-phenylacetamide, cinnamaldehyde, cinnamyl alcohol, acetophenone, indole, 3-hydroxy-1,2-dimethyl-4-pyridone, di(2-phenylethyl) ether, di(cyclopropylmethyl) ether, 3-methylcyclopent-2-enone and a synthetic precursor of nalidixic acid.


2020 ◽  
Author(s):  
Baojian Xiong ◽  
Yue Li ◽  
Yin Wei ◽  
Søren Kramer ◽  
Zhong Lian

Cross-coupling between substrates that can be easily derived from phenols is highly attractive due to the abundance and low cost of phenols. Here, we report a dual nickel/palladium-catalyzed reductive cross-coupling between aryl tosylates and aryl triflates; both substrates can be accessed in just one step from readily available phenols. The reaction has a broad functional group tolerance and substrate scope (>60 examples). Furthermore, it displays low sensitivity to steric effects demonstrated by the synthesis of a 2,2’disubstituted biaryl and a fully substituted aryl product. The widespread presence of phenols in natural products and pharmaceuticals allow for straightforward late-stage functionalization, illustrated with examples such as Ezetimibe and tyrosine. NMR spectroscopy and DFT calculations indicate that the nickel catalyst is responsible for activating the aryl triflate, while the palladium catalyst preferentially reacts with the aryl tosylate.


2009 ◽  
Vol 15 (24) ◽  
pp. 5950-5955 ◽  
Author(s):  
Thomas M. Gøgsig ◽  
Anders T. Lindhardt ◽  
Mouloud Dekhane ◽  
Julie Grouleff ◽  
Troels Skrydstrup

Synthesis ◽  
2021 ◽  
Author(s):  
Raed Al-Zoubi ◽  
Reem M. Altamimi ◽  
Walid K. Al-Jammal ◽  
Khaled Q. Shawakfeh ◽  
Mazhar S. Al-Zoubi ◽  
...  

A facile and unprecedented synthesis of 2,3-diiodinated or 2,6-diiodinated diarylether/thioether derivatives through regioselective Ullmann-type cross couplings of 5-substituted-1,2,3-triiodobenzene and phenols/thiophenols is described. Remarkably, the coupling reactions are simply controlled by the type of nucleophiles and the nature of C5 substituent at 1,2,3-triiodoarenes providing the internal or terminal coupling products in high regioselectivity and good isolated yields. Noticeable steric and electronic effects were clearly observed on both 1,2,3-triiodoarene and nucleophile. The highest yields were isolated from a combination between either electron-poor 1,2,3-triiodoarenes and phenols or electron-rich 1,2,3-triiodoarenes and thiophenols. The optimized conditions were found to be suitable for several functional groups. Using this methodology, mammary carcinoma inhibitor BTO-956 is prepared in only one step with excellent regioselectivity and good isolated yield. This report discloses the first method to make 2,3-diiodinated and 2,6-diiodinated diarylethers/thioethers in one step that is efficient, regioselective, general in scope and truly remarkable precursors for other transformations.


2015 ◽  
Vol 6 (3) ◽  
pp. 1780-1791 ◽  
Author(s):  
Samantha E. Brown-Xu ◽  
Malcolm H. Chisholm ◽  
Christopher B. Durr ◽  
Thomas F. Spilker ◽  
Philip J. Young

MM complexes as potential synthons for the development of higher order extended structures via Heck coupling reactions, exhibiting interesting photophysical properties.


2015 ◽  
Vol 6 (5) ◽  
pp. 2765-2769 ◽  
Author(s):  
Masanori Nagatomo ◽  
Daigo Kamimura ◽  
Yuki Matsui ◽  
Keisuke Masuda ◽  
Masayuki Inoue

We devised new radical-based two- and three-component coupling reactions of sugar derivatives, and realized one-step construction of contiguously substituted polyol structures.


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