Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Tokai National Higher Education and Research System, Furo-cho, Chikusa-ku, 464-8603, Nagoya, Japan.
Integrated Research Consortium on Chemical Science (IRCCS), Nagoya University, Tokai National Higher Education and Research System, Furo-cho, Chikusa-ku, 464-8602, Nagoya, Japan.
Chemistry. 2023 Feb 10;29(9):e202203280. doi: 10.1002/chem.202203280. Epub 2022 Dec 27.
Base-stabilized neutral oxoborane and thioxoborane supported by a bis(oxazolinyl)(phenyl)methanide ligand have been synthesized and structurally characterized. While previous synthetic attempts of oxoborane ligated by β-diketiminate (NacNac) did not allow for its isolation in acid-free form, oxoborane supported by a bis(oxazolinyl)(phenyl)methanide ligand is isolable, due to the absence of imine ɑ-protons and steric protection of enamine carbon. Crystallographic analysis revealed the presence of a B-O double bond close to the shortest end of the reported lengths. Its reactivity has also been examined, and it was majorly governed by the nucleophilicity and basicity of the oxygen atom. The chemical inertness and synthetic convenience of the bis(oxazolinyl)(phenyl)methanide scaffold presented in this work suggest its utility as an innocent alternative to the NacNac scaffold.
已合成并结构表征了由双（恶唑啉基）（苯基）甲烷配体稳定的中性硼基氧和硼基硫。虽然以前通过β-二酮亚胺（NacNac）配位的硼基氧的合成尝试无法在无酸形式下分离，但由于不存在亚胺α-质子和烯胺碳的空间位阻，由双（恶唑啉基）（苯基）甲烷配体稳定的硼基氧是可分离的。晶体结构分析表明存在一个 B-O 双键，接近于报道长度的最短端。还研究了其反应性，主要受氧原子的亲核性和碱性控制。本文中所提出的双（恶唑啉基）（苯基）甲烷骨架具有化学惰性和合成便利性，表明它可用作 NacNac 骨架的无害替代品。
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