Redox-Neutral Nickel-Catalyzed Selective Hydroalkynylation of Internal Alkyne and Its Application in Anticancer Agent Discovery

Weiming Chen; Teng Liu; Shuqing Li; Guangyu Li; Gaorong Wu; Youjia Gao; Zhilin Xu; Yitao Wu; Xiaopeng Peng; Jiuzhong Huang

doi:10.1002/cjoc.202400655

Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (24) : 3317 -3323. DOI: 10.1002/cjoc.202400655

Concise Report

Redox-Neutral Nickel-Catalyzed Selective Hydroalkynylation of Internal Alkyne and Its Application in Anticancer Agent Discovery

Author information +

History +

PDF

Abstract

Comprehensive Summary:Herein, an unprecedented nickel-catalyzed regioselective hydroalkynylation of unsymmetrical internal alkynes was realized with steric hindered resistance selectivity via the cyano-directing group strategy. Significantly, the resulting 1, 3-enyne products could be effectively employed in the synthesis of novel nitrogen-containing tricyclics compounds, that provided the potential candidate compound 8a (IC ₅₀ = 2.6—6.1 µmol/L) for the anti-tumor cell proliferation activity. Therefore, this work not only improves the transition-metal- catalyzed hydroalkynylation strategy of internal alkynes, but also exhibits versatility of 1, 3-enynes in the construction of the complex bioactive chemical space.

Keywords

Directing group strategy / Hydroalkynylation / 1, 3-Enynes / Dihydroindeno[2, 1-c]pyrazole / Anti-tumor candidate

Cite this article

Download citation ▾

Weiming Chen, Teng Liu, Shuqing Li, Guangyu Li, Gaorong Wu, Youjia Gao, Zhilin Xu, Yitao Wu, Xiaopeng Peng, Jiuzhong Huang. Redox-Neutral Nickel-Catalyzed Selective Hydroalkynylation of Internal Alkyne and Its Application in Anticancer Agent Discovery. Chinese Journal of Chemistry, 2024, 42(24): 3317-3323 DOI:10.1002/cjoc.202400655