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Synfacts 2025; 21(08): 788
DOI: 10.1055/a-2639-3662
Metals in Synthesis

A Light Way to Oxidize Benzylic C(sp3)–H Bonds Using Copper

Rezensent(en):
Mark Lautens 
,
Andrew G. Durant
Li F, Liu X-M, Pan J-B, Dai L, Yang Y, Xiao L-J, Fan C, Zhou Q-L *. Nankai University, Tianjin, P. R. China
Photo- and Copper-Catalyzed Enantioselective Oxidation of Benzylic C(sp3)−H Bonds.

J. Am. Chem. Soc. 2025;
147: 19093-19100
DOI: 10.1021/jacs.5c04142
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Keywords

copper - oxidation - photocatalyst - enantioselectivity

Significance

Benzylic oxidation of C(sp3)–H bonds using copper/photoredox catalysis is reported. This method represents a simple, mild method to asymmetrically generate benzylic C–O bonds. The reaction uses stoichiometric amounts of substrates, which generates no excess reagent waste, and uses di-tert-butyl peroxide as a terminal oxidant.


 

Comment

The reaction proceeds initially through oxidation of N-hydroxyphthalamide by the excited photocatalyst. The generated O-centered radical serves two purposes: (i) hydrogen atom abstraction from the benzylic position occurs forming a benzylic radical; and (ii) radical addition to the copper catalyst. Addition of the benzylic radical to the copper and reductive elimination lead to the final product.


 

 

Publikationsverlauf

Artikel online veröffentlicht:
23. Juli 2025

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