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Synfacts 2023; 19(12): 1207
DOI: 10.1055/s-0043-17635898
Metals in Synthesis

Dealkenylative C(sp3)–N Cross-Coupling of Alkenes and Amines by Merging Ozonolysis and Copper Catalysis

Contributor(s):
Martin Oestreich
,
Hendrik F. T. Klare
,
Aliyaah J. M. Rahman
He Z, Moreno JA, Swain M, Wu J, Kwon O. * University of California, Los Angeles, USA
Aminodealkenylation: Ozonolysis and Copper Catalysis Convert C(sp3)–C(sp2) Bonds to C(sp3)–N Bonds.

Science 2023;
381: 877-886
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Key words

aminodealkenylation - copper catalysis - C(sp3)–N bond formation - ozonolysis

Significance

Kwon and co-workers report a novel aminodealkenylation approach to form C(sp3)–N bonds by coupling alkenes and a diverse set of amines. The synthetic utility of this protocol is demonstrated by the preparation of complex bioactive molecules.


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Comment

α-Methylstyrene functions as an effective methylation agent within this protocol. Mechanistic investigation such as kinetic studies support the shown mechanism, involving an unusual copper ion pair cooperative process.


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Publication History

Article published online:
15 November 2023

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