Visible-light-induced nickel-catalyzed α-hydroxytrifluoroethylation of alkyl carboxylic acids: Access to trifluoromethyl alkyl acyloins

A visible-light-induced nickel-catalyzed cross coupling of alkyl carboxylic acids with N-trifluoroethoxyphthalimide is described. Under purple light irradiation, an α-hydroxytrifluoroethyl radical generated from a photoactive electron donor–acceptor complex between Hantzsch ester and N-trifluoroetho...

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Bibliographic Details
Published in:Beilstein Journal of Organic Chemistry
Main Authors: Feng Chen, Xiu-Hua Xu, Zeng-Hao Chen, Yue Chen, Feng-Ling Qing
Format: Article
Language:English
Published: Beilstein-Institut 2023-09-01
Subjects:
alkyl carboxylic acids
cross coupling
eda complex
nickel catalysis
trifluoromethyl acyloins
Online Access:https://doi.org/10.3762/bjoc.19.98
Description
Summary:A visible-light-induced nickel-catalyzed cross coupling of alkyl carboxylic acids with N-trifluoroethoxyphthalimide is described. Under purple light irradiation, an α-hydroxytrifluoroethyl radical generated from a photoactive electron donor–acceptor complex between Hantzsch ester and N-trifluoroethoxyphthalimide was subsequently engaged in a nickel-catalyzed coupling reaction with in situ-activated alkyl carboxylic acids. This convenient protocol does not require photocatalysts and metal reductants, providing a straightforward and efficient access to trifluoromethyl alkyl acyloins in good yields with broad substrate compatibility. The complex bioactive molecules were also compatible with this catalytic system to afford the corresponding products.
ISSN:1860-5397

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