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Updated: Jan 23, 2026
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Copper-Catalyzed Intermolecular [4 + 2] Annulation Enabled by Internal Oxidant-Promoted C(sp3)-H Functionalization:
Chuanle Zhu1, Hao Zeng1, Chi Liu1
1Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering , South China University of Technology , Guangzhou 510640 , P. R. China.
Abstract:
A copper-catalyzed diastereoselective [4 + 2] cyclolization of α,β-unsaturated ketoxime acetates and trifluoromethyl ketones affords various 3-trifluoromethylated 3-hydroxy-cylcohexan-1-ones smoothly. This reaction features the selective functionalization of a less acidic C(sp3)-H bond by an internal oxdative C(sp3)-H functionalization strategy. Preliminary investigations revealed that α,β-unsaturated ketoxime acetates were an internal oxidant, and the in situ generated H2O served as the O-source of the carbonyl oxygen in the product.
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