Practical Catalytic Cleavage of C(sp3)−C(sp3) Bonds in Amines
The selective cleavage of thermodynamically stable C(sp3)−C(sp3) single bonds is rare compared to their ubiquitous formation. Herein, we describe a general methodology for such transformations using homogeneous copper‐based catalysts in the presence of air. The utility of this novel methodology is d...
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Veröffentlicht in: | Angewandte Chemie International Edition 2019-07, Vol.58 (31), p.10693-10697 |
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Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | The selective cleavage of thermodynamically stable C(sp3)−C(sp3) single bonds is rare compared to their ubiquitous formation. Herein, we describe a general methodology for such transformations using homogeneous copper‐based catalysts in the presence of air. The utility of this novel methodology is demonstrated for Cα−Cβ bond scission in >70 amines with excellent functional group tolerance. This transformation establishes tertiary amines as a general synthon for amides and provides valuable possibilities for their scalable functionalization in, for example, natural products and bioactive molecules.
Cutting with air: C(sp3)−C(sp3) single bonds in amines can be cleaved using homogeneous copper‐based catalysts in the presence of air. The utility of this novel methodology is demonstrated for Cα−Cβ bond scission in >70 amines with excellent functional group tolerance. |
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ISSN: | 1433-7851 1521-3773 1521-3773 |
DOI: | 10.1002/anie.201903019 |