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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)
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
Yan Dang , Chaohong Jia , Yalan Wang , Li Wang , Yafei Li , Yahong Li . 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[J]. Chinese Journal of Organic Chemistry, 2023 , 43(3) : 1124 -1135 . DOI: 10.6023/cjoc202211038
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