Citation: Yuchuan Zhu, Kaili Xie, Yufei Li, Fang Liu, Yucheng Gu, Qingmin Wang, Weihua Zhang, Qing Xia. Alkyl halides dictate site selectivity in aromatic nitrile alkylations[J]. Chinese Chemical Letters, ;2026, 37(7): 111819. doi: 10.1016/j.cclet.2025.111819 shu

Alkyl halides dictate site selectivity in aromatic nitrile alkylations

Yuchuan Zhu ^a ,
Kaili Xie ^a ,
Yufei Li ^a ,
Fang Liu ^a ,
Yucheng Gu ^b ,
Qingmin Wang ^c ,
Weihua Zhang ^{a, *,} ,
Qing Xia ^{a, *,}

a.
Jiangsu Key Laboratory of Pesticide Science, Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, China
b.
Syngenta Jealott's Hill International Research Centre RG42 6EY, United Kingdom
c.
State Key Laboratory of Elemento-OrganicChemistry, Research Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin 300071, China

zhwh@njau.edu.cn

xiaq@njau.edu.cn

Received Date: 12 June 2025
Revised Date: 18 August 2025
Accepted Date: 2 September 2025
Available Online: 10 September 2025

Figures(6)

Alkylated arenes, which are prevalent molecular building blocks, are widely applicable across various scientific domains. However, regioselectively alkylating arenes often poses significant challenges, despite their apparent simplicities. Herein, we report the first examples of substrate-controlled photocatalyzed regiodivergent alkylations of aromatic nitriles. The judicious choice of alkyl halide facilitated selection of mechanistically divergent processes. The two reaction manifolds, an ipso-substitution path that proceeds via radical coupling and a Friedel−Crafts-type C–H alkylation via quantum mechanical tunneling, enabled selective access to regioisomeric alkylated arenes. Mechanistic investigations combined with density functional theory (DFT) calculations shed light on the origin of this regioselectivity switch. Remarkably, this process exhibited superior efficiencies, reactivities, and synthetic utilities, and can be performed on the gram scale.
- Alkylation,
- Regioselectivity,
- Photocatalysis,
- Halogen atom transfer,
- Quantum mechanical tunneling
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