Triborane (B3H7)-mediated regioselective substitution reactions of pyridine derivatives,Chemical Science

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Triborane (B3H7)-mediated regioselective substitution reactions of pyridine derivatives
Chemical Science ( IF 7.6 ) Pub Date : 2024-07-26 , DOI: 10.1039/d4sc03109a
Zi-Heng Fan ₁ , Jia-Xin Kang ₁ , Sihan Jia ₁ , Qiao-Jing Pan ₁ , Lei Cao ₁ , Xi-Meng Chen ₁ , Cong-Qiao Xu ₂ , Yan-Na Ma ₃ , Xuenian Chen _{1,

3}

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There exists an interplay between borane and a Lewis base in their adducts. However, studies on these adducts so far have mainly focused on the different reactions of B–H bonds with limited attention given to the influence of borane on the chemistry of the Lewis base, except for BF₃ and BAr₃. Herein, we have synthesized novel borane adducts with pyridine derivatives, Py·B₃H₇, in which the coordination of B₃H₇ efficiently achieved the intra-molecular charge transfer. The strong B–N bond in these adducts resulted in the formation of stable dearomatic intermediates of pyridine derivatives, confirmed by ¹H and ¹¹B NMR spectroscopy, from which different reactions have transpired to realize C(sp³)–H and C(sp²)–H functionalization under mild conditions. The B₃H₇ pyridine derivatives are stable and do not dissociate or decompose during the reaction process. The high stability of the B–N bond makes this method a good option for boron-containing drugs with potential for use in boron neutron capture therapy (BNCT).

中文翻译：

三硼烷 (B3H7) 介导的吡啶衍生物的区域选择性取代反应

硼烷和路易斯碱在其加合物中存在相互作用。然而，迄今为止，对这些加合物的研究主要集中在B-H键的不同反应上，而很少关注硼烷对路易斯碱化学的影响，除了BF ₃和BAr ₃ 。在此，我们合成了新型硼烷与吡啶衍生物的加合物Py·B ₃ H ₇ ，其中B ₃ H ₇的配位有效地实现了分子内电荷转移。这些加合物中的强 B-N 键导致吡啶衍生物的稳定脱芳族中间体的形成，经¹ H 和¹¹ B NMR 光谱证实，其中发生了不同的反应，实现了 C(sp ³ )–H 和 C(sp ² )–H在温和条件下官能化。 B ₃ H ₇吡啶衍生物稳定，在反应过程中不会解离或分解。 B-N 键的高稳定性使得该方法成为含硼药物的良好选择，并有可能用于硼中子捕获疗法 (BNCT)。

更新日期：2024-07-26

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