Citation: Tian-Zhang Wang, Le-Yu Tang, Yu-Qiu Guan, Lingfei Hu, Gang Lu, Yu-Feng Liang. Nickel-catalyzed reductive alkynylation of ketoimines via unstrained C–C bond activation[J]. Chinese Chemical Letters, ;2025, 36(11): 111050. doi: 10.1016/j.cclet.2025.111050 shu

Nickel-catalyzed reductive alkynylation of ketoimines via unstrained C–C bond activation

Tian-Zhang Wang ^a ,
Le-Yu Tang ^{a, b} ,
Yu-Qiu Guan ^a ,
Lingfei Hu ^a ,
Gang Lu ^{a, *,} ,
Yu-Feng Liang ^{a, *,}

a.
School of Chemistry and Chemical Engineering, Shandong University, Ji'nan 250100, China
b.
Institut Parisien de Chimie Moléculaire, CNRS UMR 8232, Université Pierre et Marie Curie-Sorboone Universite, Paris 75005, France

ganglu@sdu.edu.cn

yfliang@sdu.edu.cn

Received Date: 24 November 2024
Revised Date: 6 March 2025
Accepted Date: 6 March 2025
Available Online: 8 March 2025

Figures(6)

The carbon–carbon bond is the one of the most fundamental and abundant bonds that exist in organic molecules, and the challenge of functionalization of carbon–carbon bond has always been a critical pursuit in organic synthesis. In recent years, there have been a growing number of studies on the C–C bond activation. Nevertheless, the metal-catalyzed cleavage of the C–C(O) bond in unstrained ketones has remained relatively underexplored due to the strong affinity of carbonyl groups for metals. In this study, we report a nickel-catalyzed strategy for the reductive alkynylation of ketoimines via β-carbon elimination. This method involves the conversion of aryl ketones into aryl ketoimines, thus expanding the toolbox of aryl electrophiles. The use of a N-heterocyclic carbene (NHC) ligand is crucial for this catalytic transformation. This discovery leads to a cross electrophile coupling reaction characterized by its operational simplicity, unique chemo-selectivity and excellent functional group tolerance. In addition, the approach has been effectively applied to the late-stage alkynylation of diverse pharmaceuticals. Ultimately, a series of comprehensive experiments and theoretical studies were conducted to provide insights into the reaction pathway, which supports the proposed β-carbon elimination process.
- Unstrained C–C bond activation,
- β-Carbon elimination,
- Nickel catalyst,
- Cross electrophile coupling,
- Alkynylation
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沈阳化工大学材料科学与工程学院沈阳 110142