Citation: Xinlong Han, Huiying Zeng, Chao-Jun Li. Trifluoromethylative homo-coupling of carbonyl compounds[J]. Chinese Chemical Letters, ;2025, 36(1): 109817. doi: 10.1016/j.cclet.2024.109817 shu

Trifluoromethylative homo-coupling of carbonyl compounds

Xinlong Han ^a ,
Huiying Zeng ^{a, *,} ,
Chao-Jun Li ^{b, *,}

a.
The State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China
b.
Department of Chemistry, FQRNT Centre for Green Chemistry and Catalysis, McGill University, Montreal, Quebec, H3A 0B8, Canada

zenghy@lzu.edu.cn

cj.li@mcgill.ca

Received Date: 6 January 2024
Revised Date: 20 March 2024
Accepted Date: 22 March 2024
Available Online: 22 March 2024

Figures(6)

Carbonyl compounds are abundant in nature and represent a substantial portion of biomass resources. Despite significant recent progress in homo-coupling of carbonyl compounds, achieving their deoxy-functionalization homo-coupling remains a highly intricate challenge. Herein, we report an entirely novel reaction paradigm: the trifluoromethylative homo-coupling of carbonyl compounds via hydrazones, which enables the formation of three C(sp³)–C(sp³) bonds in a single step. This method provides a new pathway for synthesizing trifluoromethylative coupling product which has unique applications in both fields of medical and material sciences. Mechanistic investigations have unveiled that the formation of a trifluoromethyl-substituted benzyl radical plays a pivotal role as a key intermediate in this reaction.
- Carbonyl compounds,
- Trifluoromethylation,
- Homo-coupling,
- C(sp³)–C(sp³) bond formation
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