Citation: Xiuping Yuan, Jiamin Yuan, Jiaqiong Sun, Jianjun Yin, Simin Wang, Dazhen Shi, Shucheng Ma, Xiaoyu Li, Qian Zhang, Tao Xiong. Copper-catalyzed borylcyanation of unactivated alkenes via cyano group translocation[J]. Chinese Chemical Letters, ;2026, 37(12): 112422. doi: 10.1016/j.cclet.2026.112422 shu

Copper-catalyzed borylcyanation of unactivated alkenes via cyano group translocation

Xiuping Yuan ^{a, 1} ,
Jiamin Yuan ^{a, 1} ,
Jiaqiong Sun ^{a, *,} ,
Jianjun Yin ^a ,
Simin Wang ^a ,
Dazhen Shi ^a ,
Shucheng Ma ^a ,
Xiaoyu Li ^a ,
Qian Zhang ^{a, b} ,
Tao Xiong ^{a, *,}

a.
Province Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Changchun 130024, China
b.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

sunjq295@nenu.edu.cn

xiongt626@nenu.edu.cn

Received Date: 30 September 2025
Revised Date: 4 January 2026
Accepted Date: 15 January 2026
Available Online: 16 January 2026

Figures(6)

The translocation of a functional group (FG) within a molecule has perceived as a powerful strategy in synthetic chemistry, providing a unique and economic approach to molecular structure modification. Despite substantial advances, the translocation of such functional groups, such as cyano group, still heavily relies on radical-involved pathways. In contrast, the mechanically complementary polar FGs translocation remains far less underdeveloped. Herein, we report an unprecedented copper-catalyzed borylcyanation of unactivated alkenes via polar cyano group translocation. This reaction proceeds under exceptionally mild conditions with high regioselectivity and excellent functional group tolerance, affording valuable borylcyanation products containing 1,n-dinitrile motifs from readily available starting materials. The transformation is proposed to initiate through borocupration of the unactivated alkene, followed by an intramolecular addition of the resulting alkyl-copper intermediate to C≡N bond and sub-sequent β-carbon elimination. The success of this methodology is attributed to the discovery of a bidentate phosphine-ligated copper catalyst, exerting precise regioselectivity and effectively suppressing the competing rapid protonation of in-situ formed alkyl- and iminocopper intermediates by an alcohol.
- Cu catalysis,
- Borylcyanation,
- Unactivated alkenes,
- Polar cyano translocation,
- 1,n-Dinitriles
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沈阳化工大学材料科学与工程学院沈阳 110142