含吡咯基配体的锌、锂和镁配合物的合成与表征及其对芳基碘代物的硼化反应和醛、酮的硼氢化反应的催化作用
收稿日期: 2022-11-29
修回日期: 2023-01-04
网络出版日期: 2023-02-07
基金资助
国家自然科学基金(21772140); 国家自然科学基金(22171198); 江苏省高等学校优势学科建设和苏州市基础科技(SZS201905)
Synthesis and Characterization of Zinc, Lithium and Magnesium Complexes Containing Pyrrolyl Ligands, and Utilization as Catalysts in Borylation of Aryl Iodides and Hydroboration of Aldehydes and Ketones
Received date: 2022-11-29
Revised date: 2023-01-04
Online published: 2023-02-07
Supported by
National Natural Science Foundation of China(21772140); National Natural Science Foundation of China(22171198); Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institution, and the Project of Scientific and Technologic Infrastructure of Suzhou(SZS201905)
用ZnEt2分别与两个含吡咯基的配体2-(2-((((1H-吡咯-2-基)亚甲基)氨基)甲基)-1H-吡咯-1-基)-N,N-二甲基乙烷-1-胺(HL1)和N-((1H-吡咯-2-甲基)甲基)-1-(1H-吡啶-2-基)甲亚胺(H2L2)反应, 合成了两个化合物[Zn(L1)Et] (1)和[Zn2(L2)2(THF)2] (2). 通过核磁共振波谱、元素分析和单晶X射线衍射对配合物进行了表征. 研究了配合物1和2对芳基碘与B2Pin2 (B2Pin2=4,4,4',4',5,5,5',5'-八甲基-2,2′-双(1,3,2-二氧杂硼烷))偶联反应的催化作用. 它们都对这类硼化反应有催化活性. 化合物1显示出比2更高的活性. 化合物1催化的这类硼化反应具有温和的条件、宽的底物范围和较好的官能团相容性的特点. 此外, 还研究了先前报道的两种已知化合物[Li2(L1)2] (3)和[Mg(L1)2(THF)2] (4)对频哪硼烷(HBpin)和醛、酮的硼氢化反应的催化作用. 配合物3和4对该类反应具有较好的催化活性, 在很短的时间内以优异的产率生成了一系列硼酸酯.
党燕 , 贾朝红 , 王亚兰 , 王丽 , 李亚飞 , 李亚红 . 含吡咯基配体的锌、锂和镁配合物的合成与表征及其对芳基碘代物的硼化反应和醛、酮的硼氢化反应的催化作用[J]. 有机化学, 2023 , 43(3) : 1124 -1135 . DOI: 10.6023/cjoc202211038
The reactions of ZnEt2 with two pyrrolyl ligands 2-(2-((((1H-pyrrol-2-yl)methylene)amino)methyl)-1H-pyrrol-1- yl)-N,N-dimethylethan-1-amine (HL1) and N-((1H-pyrrol-2-yl)methyl)-1-(1H-pyrrol-2-yl)methanimine (H2L2) generated a zinc ethyl compound [Zn(L1)Et] (1) and a dinuclear complex [Zn2(L2)2(THF)2] (2). The complexes were characterized by 1H NMR, 13C NMR, elemental analysis, and single-crystal X-ray diffraction. Complexes 1 and 2 were employed as catalysts for the borylation of aryl iodides with B2Pin2 (B2Pin2=4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane)). They were both active for this coupling reaction. Complex 1 displays higher activity than that of 2. This borylation transformation promoted by 1 features mild condition, wide substrate scope and high functional group compatibility. Moreover, the catalytic activities of two known compounds previously reported by our group, namely, [Li2(L1)2] (3) and [Mg(L1)2(THF)2] (4), toward borylation of aryl iodides with B2Pin2 were also explored. They cannot catalyze this coupling reaction. Nevertheless, complexes 3 and 4 were catalytically active toward hydroboration of aldehydes and ketones by pinacolborane (HBpin), giving a variety of borate esters in excellent yields in a very short time.
Key words： borylation; hydroboration; zinc complexes; catalysis
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