Metal-Catalyzed Intermolecular Hydrofunctionalization of Allenes: Easy Access to Allylic Structures via the Selective Formation of C–N, C–C, and C–O Bonds
| Autor: | Rémi Blieck, Florian Monnier, Marc Taillefer |
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| Přispěvatelé: | Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC) |
| Rok vydání: | 2020 |
| Předmět: |
Allylic rearrangement
010405 organic chemistry Chemistry Intermolecular force Leaving group Context (language use) General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry 0104 chemical sciences Catalysis Nucleophile Electrophile [CHIM]Chemical Sciences Molecule ComputingMilieux_MISCELLANEOUS |
| Zdroj: | Chemical Reviews Chemical Reviews, American Chemical Society, 2020, 120 (24), pp.13545-13598. ⟨10.1021/acs.chemrev.0c00803⟩ |
| ISSN: | 1520-6890 0009-2665 |
| DOI: | 10.1021/acs.chemrev.0c00803 |
| Popis: | Following a strong regain of interest over the past 20 years in the chemistry of allenes, this "forgotten" family of unsaturated molecules is undergoing a renaissance. In this context, the metal-catalyzed hydrofunctionalization of allenes is nowadays one of the most studied transformations. The latter is of great interest because it opens a way to produce selectively functionalized allylic structures. These motifs are important in synthesis, particularly for the formation of asymmetric centers. Hydrofunctionalization of allenes is also a totally atom economical strategy, avoiding generation of any waste, to produce allylic functionalized structures. Compared to the main pathway to obtain the latter (aka Tsuji-Trost allylic substitution), metal-catalyzed hydrofunctionalization does not require the prefunctionalization of starting material with a leaving group. This review presents a state of the art exploration of all existing transition metal-catalyzed methods allowing the selective intermolecular hydrofunctionalization of allenes with N-H, C-H, and O-H nucleophiles or electrophiles. |
| Databáze: | OpenAIRE |
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