苄叉丙酮、硒粉和硼氢化钠一锅法构建四氢-2H-硒吡喃衍生物
收稿日期: 2023-11-20
修回日期: 2023-12-27
网络出版日期: 2024-01-18
基金资助
山西省自然科学基金(20210302124072); 山西省自然科学基金(202203021222318); 山西省自然科学基金(202103021223386); 山西省高等学校科技创新(2021L568)
One-Pot Synthesis of Tetrahydro-2H-selenopyran Derivatives from Benzalacetones, Elemental Selenium, and Sodium Borohydride
Received date: 2023-11-20
Revised date: 2023-12-27
Online published: 2024-01-18
Supported by
Natural Science Foundation of Shanxi Province(20210302124072); Natural Science Foundation of Shanxi Province(202203021222318); Natural Science Foundation of Shanxi Province(202103021223386); Program for the Innovative Talents of Higher Education Institutions of Shanxi(2021L568)
报道了一种以苄叉丙酮、硒粉和硼氢化钠为原料, 采用一锅法合成一系列四氢-2H-硒吡喃衍生物的新方法. 此反应通过形成6个新的化学键很好的构建一系列含硒六元环. 得到了20个含有四氢-2H-硒吡喃结构的小分子化合物, 最高产率可达91%. X单晶衍射分析表明四氢-2H-硒吡喃六元环与环己烷具有类似的空间立体结构, 呈现出稳定的椅式构象. 此反应在克量级规模下依然可以顺利进行. 可能的反应机理表明此反应为涉及双Michael加成/二硒键的断裂/Mi- chael加成/Aldol反应的多步串级反应. 此方法具有底物适应性强、不使用过度金属催化剂以及反应条件温和的特点.
陈栋栋 , 杨旭锋 . 苄叉丙酮、硒粉和硼氢化钠一锅法构建四氢-2H-硒吡喃衍生物[J]. 有机化学, 2024 , 44(5) : 1641 -1648 . DOI: 10.6023/cjoc202311017
A reaction has been developed to synthesize a series of tetrahydro-2H-selenopyran derivatives from benzalace- tones, sodium borohydride, and elemental selenium by one-pot method. The reaction proceeds well to construct a tetrahydro-2H-selenopyran ring and six new bonds. Twenty tetrahydro-2H-selenopyran derivatives were obtained, and the yield was up to 91%. The X-ray single crystal analysis showed that this selenium-containing heterocyclic ring exists as a stable chair conformation similar to cyclohexane. The reaction works well when scaled up to the gram scale. A possible mechanism was proposed, involving hydrogenation of selenium/double Michael addition/cleavage of diselenide bond/Michael addition/Aldol reaction. This reaction is characterized by high compatibility to substrates, transition-metal free, and mild reaction conditions.
Key words： tetrahydro-2H-selenopyran; cyclization; elemental selenium; one-pot; benzalacetones
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