Article: Palladium-Catalyzed Aryl Amination Reactions of 6-Bromo- and 6-Chloropurine Nucleosides.
Advanced synthesis & catalysis
2011 Volume 352, Issue 10, Page(s) 1728–1735
Abstract: ... detailed analysis of aryl amination reactions of 6-chloropurine nucleosides, and comparison of the two ... Palladium-catalyzed C-N bond forming reactions of 6-bromo- as well as 6-chloropurine ... with Pd(OAc)(2)/Xantphos/Cs(2)CO(3), in PhMe at 100 °C. Reactions of the bromo nucleoside derivatives ...
| Abstract | Palladium-catalyzed C-N bond forming reactions of 6-bromo- as well as 6-chloropurine ribonucleosides and the 2'-deoxy analogues with aryl amines are described. Efficient conversions were observed with Pd(OAc)(2)/Xantphos/Cs(2)CO(3), in PhMe at 100 °C. Reactions of the bromo nucleoside derivatives could be conducted at a lowered catalytic loading (5 mol % Pd(OAc)(2)/7.5 mol % Xantphos), whereas good product yields were obtained with a higher catalyst load (10 mol % Pd(OAc)(2)/15 mol % Xantphos) when the chloro analogue was employed. Among the examples evaluated, silyl protection for the hydroxyls appears better as compared to acetyl. The methodology has been evaluated via reactions with a variety of aryl amines and by synthesis of biologically relevant deoxyadenosine and adenosine dimers. This is the first detailed analysis of aryl amination reactions of 6-chloropurine nucleosides, and comparison of the two halogenated nucleoside substrates. |
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| Keywords | covid19 |
| Language | English |
| Publishing date | 2011-07-26 |
| Publishing country | Germany |
| Document type | Journal Article |
| ZDB-ID | 2041384-1 |
| ISSN | 1615-4169 ; 1615-4150 |
| ISSN (online) | 1615-4169 |
| ISSN | 1615-4150 |
| DOI | 10.1002/adsc.200900728 |
| Database | MEDical Literature Analysis and Retrieval System OnLINE |
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