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Updated: Jul 7, 2026
Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
Published on: November 21, 2017
O-Alkylisourea-Enabled Nickel/Photoredox-Catalyzed Giese Reaction
Weikang Xiong1, Fangxuan Ba1, Tengfei Kang1
1Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, People's Republic of China.
Abstract:
The Giese reaction is one of the most widely employed carbon-carbon (C-C) bond-forming reactions in synthetic chemistry. In particular, the generation of alkyl radicals via photocatalytic deoxygenation of alcohols under mild conditions is synthetically appealing. Herein, we report an efficient nickel/photoredox-catalyzed Giese reaction of alcohol-derived O-alkylisoureas with a range of Michael acceptors, using an inexpensive diaryl ketone as the photocatalyst. Notably, the system successfully transforms secondary, tertiary, and especially primary alcohols into the target products in moderate to good yields. Mechanistic studies suggest that the formation of an alkyl halide intermediate, via nucleophilic substitution of the O-alkylisourea with the nickel catalyst, is the key step for radical generation.
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