Transition metal-free Csp3-Csp3 bond-forming reactions of N-tosylaziridines and gem-diborylalkanes

Pu-Zhang Zi , Quan-Hong Zhao , Zhan-Cai Ma , Xiao-Lin Ren , Xing-Bang Liu , Yi-Wei Qiao , Lin-Wen Wei , Song Liu , Yuan Huang
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Abstract

The incorporation of additional Csp3 atoms into candidate drugs may enhance their pharmacological properties. Nevertheless, it remains challenging to construct desired Csp3-Csp3 bonds efficiently and practically. The present article reports a novel Csp3-Csp3 bond-forming reaction of 2-aryl/alkyl substituted aziridines with gem-diborylalkanes under tranisiton metal free conditions. A wide range of γ-gem-diboronate esters substituted amines can be accessed in good yield and regioselectivity. The results demonstrated that various aziridines could react with gem-diborylalkanes in the presence of LiTMP as the base within 15 ​min at ambient temperature.

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n - tosyziridine和gem-二硼烷的无过渡金属Csp3-Csp3成键反应
在候选药物中加入额外的Csp3原子可以增强其药理学性质。然而,如何高效、实用地构建理想的Csp3-Csp3键仍然是一个挑战。本文报道了在无过渡金属条件下,2-芳基/烷基取代氮杂环与宝石二硼烷的Csp3-Csp3成键反应。广泛的γ-宝石二硼酸酯取代胺具有良好的收率和区域选择性。结果表明,在常温条件下,以LiTMP为底物存在的情况下,各种氮杂环类化合物均可与宝石二硼烷在15 min内发生反应。
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