Cobalt-Catalyzed Allylic C(sp3)–H Carboxylation with CO2
| Autor: | Tsuyoshi Mita, Kenichi Michigami, Yoshihiro Sato |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
Allylic rearrangement Ketone 010405 organic chemistry Xantphos Regioselectivity General Chemistry 010402 general chemistry 01 natural sciences Biochemistry Catalysis 0104 chemical sciences chemistry.chemical_compound Colloid and Surface Chemistry chemistry Carboxylation Amide Organic chemistry Sharpless asymmetric dihydroxylation |
| Zdroj: | Journal of the American Chemical Society. 139:6094-6097 |
| ISSN: | 1520-5126 0002-7863 |
| DOI: | 10.1021/jacs.7b02775 |
| Popis: | Catalytic carboxylation of the allylic C(sp3)–H bond of terminal alkenes with CO2 was developed with the aid of a Co/Xantphos complex. A wide range of allylarenes and 1,4-dienes were successfully transformed into the linear styrylacetic acid and hexa-3,5-dienoic acid derivatives in moderate to high yields, with excellent regioselectivity. The carboxylation showed remarkable functional group tolerability, so that selective addition to CO2 occurred in the presence of other carbonyl groups such as amide, ester, and ketone. Since styrylacetic acid derivatives can be readily converted into optically active γ-butyrolactones through Sharpless asymmetric dihydroxylation, this allylic C(sp3)–H carboxylation showcases a facile synthesis of γ-butyrolactones from simple allylarenes via short steps. |
| Databáze: | OpenAIRE |
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