| Selective Hydrogenation of Avermectin Catalyzed by Iridium-Phosphine Complexes |
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| 作者姓名： | 马晓艳 王堃 张磊 李贤均 李瑞祥 |
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| 作者单位： | Education Ministry Key Laboratory of Green Chemistry ＆ Technology, College of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China |
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| 基金项目： | Project supported by the National Natural Science Foundation of China （Nos. 20371032 and 20271035） and the Student Innovation Fund of Sichuan University. |
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| 摘 要： | A series of new iridium complexes, IrCl（COD）（TMOPP） （1） COD=1,5-cyclooctadiene, TMOPP=tris（4- methoxyphenyl）phosphine], IrCl（COD）（TFMPP） （2） TFMPP = tris（4-trifluoromethylphenyl）phosphine], IrCl（COD）（BDNA） （3） BDNA= 1,8-bis（diphenylphosphinomethyl）naphthalene], IrCl（COD）（BISBI） （4） BISBI= 2,2＇-bis（diphenylphosphinomethyl）biphenyl] and IrCl（COD）（BDPB） （5） BDPB= 1,2-bis（diphenylphosphinomethyl）benzene], were synthesized and characterized by NMR spectra and elemental analyses. In order to obtain the relationships between complex structures and their catalytic properties, IrCl（COD）（DPPM） （6） DPPM = bis（diphenylphosphino）methane], IrCl（COD）（DPPE） （7） DPPE= 1,2-bis（diphenylphosphino）ethane], IrCl（COD）（DPPP） （8） DPPP=1,3-bis（diphenylphosphino）propane] and IrCl（COD）（TPP） （9） TPP=triphenylphosphine], were also synthesized according to the reported methods. The hydrogenation results showed that the low electronic density at the central metal was favorable to increase the catalytic activity for the hydrogenation of avermectin, but decrease the selectivity to ivermectin. The complex with a large chelating ring and a bulky chelating backbone would easily cause the cleavage of C-O bond in avermectin to give a byproduct avermectin aglycon.
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| 关 键 词： | 铱 磷化氢 复合物 选择加氢 催化反应 |
| 修稿时间： | 2007-02-07 |
Selective Hydrogenation of Avermectin Catalyzed by Iridium-Phosphine Complexes |
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| MA, Xiao-Yan WANG, Kun ZHANG, Lei LI, Xian-Jun LI, Rui-Xiang.Selective Hydrogenation of Avermectin Catalyzed by Iridium-Phosphine Complexes[J].Chinese Journal of Chemistry,2007,25(10):1503-1507. |
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| Authors: | MA Xiao-Yan WANG Kun ZHANG Lei LI Xian-Jun LI Rui-Xiang |
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| Institution: | 1. Education Ministry Key Laboratory of Green Chemistry & Technology, College of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China;2. Tel.: 0086‐028‐85417521;3. Fax: 0086‐028‐85412904 |
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| Abstract: | A series of new iridium complexes, IrCl(COD)(TMOPP) ( 1 ) COD=1,5‐cyclooctadiene, TMOPP=tris(4‐ methoxyphenyl)phosphine], IrCl(COD)(TFMPP) ( 2 ) TFMPP=tris(4‐trifluoromethylphenyl)phosphine], IrCl‐ (COD)(BDNA) ( 3 ) BDNA=1,8‐bis(diphenylphosphinomethyl)naphthalene], IrCl(COD)(BISBI) ( 4 ) BISBI=2,2′‐bis(diphenylphosphinomethyl)biphenyl] and IrCl(COD)(BDPB) ( 5 ) BDPB=1,2‐bis(diphenylphosphinometh‐ yl)benzene], were synthesized and characterized by NMR spectra and elemental analyses. In order to obtain the relationships between complex structures and their catalytic properties, IrCl(COD)(DPPM) ( 6 ) DPPM=bis(diphenylphosphino)methane], IrCl(COD)(DPPE) ( 7 ) DPPE=1,2‐bis(diphenylphosphino)ethane], IrCl(COD)(DPPP) ( 8 ) DPPP=1,3‐bis(diphenylphosphino)propane] and IrCl(COD)(TPP) ( 9 ) TPP=triphenylphosphine], were also synthesized according to the reported methods. The hydrogenation results showed that the low electronic density at the central metal was favorable to increase the catalytic activity for the hydrogenation of avermectin, but decrease the selectivity to ivermectin. The complex with a large chelating ring and a bulky chelating backbone would easily cause the cleavage of C? O bond in avermectin to give a byproduct avermectin aglycon. |
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| Keywords: | iridium complex phosphine avermectin hydrogenation ivermectin |
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