Synthesis of Functionalized [3], [4], [5] and [6]Dendralenes through Palladium‐Catalyzed Cross‐Couplings of Substituted Allenoates
| Autor: | Daniel J. Lippincott, Bruce H. Lipshutz, Roscoe T. H. Linstadt, Michael R. Maser |
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| Rok vydání: | 2016 |
| Předmět: |
Reaction conditions
010405 organic chemistry chemistry.chemical_element Regioselectivity General Medicine General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences chemistry.chemical_compound chemistry Nucleophile Organic chemistry Dendralene Boron Palladium |
| Zdroj: | Angewandte Chemie International Edition. 56:847-850 |
| ISSN: | 1521-3773 1433-7851 |
| DOI: | 10.1002/anie.201609636 |
| Popis: | A mild method for the synthesis of highly functionalized [3]-[6]dendralenes is reported, representing a general strategy to diversely substituted higher homologues of the dendralenes. The methodology utilizes allenoates bearing various substitution patterns, along with a wide range of boron and alkenyl nucleophiles that couple under palladium catalysis leading to sp-, sp2 -, and sp3 -substituted arrays. Regioselective transformations of the newly formed unsymmetrical dendralene derivatives are demonstrated. The use of micellar catalysis, where water is the global reaction medium, and room temperature reaction conditions, highlights the green nature of this technology. |
| Databáze: | OpenAIRE |
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