Citation: Fuyang Yue, Mingxing Li, Fei Yuan, Hongjian Song, Yuxiu Liu, Qingmin Wang. Deboronative cross-coupling enabled by nickel metallaphotoredox catalysis[J]. Chinese Chemical Letters, ;2025, 36(12): 111053. doi: 10.1016/j.cclet.2025.111053 shu

Deboronative cross-coupling enabled by nickel metallaphotoredox catalysis

State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin 300071, China

wangqm@nankai.edu.cn

Received Date: 8 January 2025
Revised Date: 26 February 2025
Accepted Date: 6 March 2025
Available Online: 7 March 2025

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With advances in organoboron chemistry, boron-centered functional groups, especially alkyl boronic acids, which are widely available, bench stable, easy to prepare, minimally toxic, and structurally diverse, have become increasingly attractive. However, their utility is limited by their high oxidation potentials. In this study, we overcame this limitation by complexing an inorganic base (K₃PO₄) with alkyl boronic acids to decrease their oxidation potentials. Specifically, we present a powerful method for light-mediated deboronative cross-coupling reactions between alkyl boronic acids and aryl halides to afford products. This method demonstrated good functional group tolerance, and the mild conditions enabled the functionalization of drug molecules. In addition, the method could be extended to three-component carboacylation/carboarylation reactions of olefins to give products with high enantiomeric excess. Moreover, the reactions could be carried out under continuous-flow conditions, which enhanced the scalability, safety, and overall efficiency of the method.
- Deboronative,
- Metallaphotoredox,
- Enantioselective,
- Radicals,
- Nickel
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