功能化膦配体的合成及在偶联反应中的应用研究
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摘要
过渡金属催化的交叉偶联反应是最有效的形成C(aryl)-C(aryl),C(aryl)-N,C(aryl)-O键的方法之一,已在有机合成中广泛应用。它在有机合成中重要性主要来自多个领域,从天然产物的合成到材料化学。发展膦配体对过渡金属催化反应有重要推动作用,近来更多的研究倾向于开发能催化具有挑战性的底物的新催化体系。本文主要研究了联咪唑膦配体的合成及在交叉偶联反应中的应用。
(1)从联咪唑出发,与3-溴丙基二苯基膦酸酯发生亲核取代反应生成1-丙基二苯基氧膦-2,2’-联咪唑,1-丙基二苯基氧膦-2,2’-联咪唑经过氢化铝锂还原反应生成配体L1——1-丙基二苯基氧膦-2,2’-联咪唑,1-丙基二苯基膦-2,2’-联咪唑经硫氧化生成配体L2——1-丙基二苯基硫膦-2,2’-联咪唑。
(2)从联咪唑出发,与3-溴丙基二苯基膦酸酯发生亲核取代反应生成1,1’-二(丙基二苯基氧膦)-2,2’联咪唑,1,1’-二(丙基二苯基氧膦)-2,2’联咪唑经过氢化铝锂还原反应生成配体L3——1,1’-二(丙基二苯基膦)-2,2’联咪唑经硫氧化生成配体L4——1,1’-二(丙基二苯基硫膦)-2,2’联咪唑。
(3)从联咪唑出发,与碘代正丁烷发生亲核取代反应生成1,1’-二丁基-2,2’联咪唑,1,1’-二丁基-2,2’联咪唑经过3-溴丙基二苯基膦酸酯取代反应生成离子液体联咪唑氧膦。
(4)把配体L1,L2,L3,L4分别应用在催化Suzuki反应和Heck反应中,实验结果表明,配体L3在催化Suzuki反应和Heck反应中都具有优越的催化活性和选择性,配体L1在催化Suzuki反应中表现出中等活性,而催化Heck反应活性较差,配体L4在催化碘代芳烃的Suzuki反应中能得到较高的产率。但配体L2催化Suzuki反应的产率则很低,配体L2和配体L4几乎都不能有效的催化Heck反应。
Transition metal-mediated cross-coupling reactions are one of the most efficient methods for the construction of C(aryl)-C(aryl), C(aryl)-N,C(aryl)-Obonds and have found widespread use in organic synthesis. Its importance in organic synthesis is evident from its application in a number of areas, ranging from natural product synthesis to materials chemistry. The development of phosphane ligands has had a huge impact in transition-metal-catalyzed reactions. Much recent work has been directed toward the development of new catalyst systems that efficiently process challenging substrates. In this paper, synthesis of functionalized phosphine ligands and their application to cross-coupling reactions have been studied.
(1) 1- 3-( diphenylphosphono)propyl-2,2’-biimidazole was synthesized by nucleophilic substitution reaction between 2,2’-biimidazole and 3-bromine propyl diphenylphosphono in high yields. 1- 3-( diphenylphosphono)propyl-2,2’-biimidazole were deoxidized by LiAlH4 to yield 1,1’-di[3-(diphenylphosphino)propyl]-2,2’-biimidazole(L1) . 1- 3-( Phosphorodithioic)propyl-2,2’-biimidazole(L2) was efficiently synthesized by Sulfur oxidationin of 1,1’-di[3-(diphenylphosphino)propyl]-2,2’-biimidazole in good yields.
(2) 1,1’-di[3-( diphenylphosphono)propyl]-2,2’-biimidazole was synthesized by nucleophilic substitution reaction between 2,2’-biimidazole and 3-bromine propyl diphenylphosphono in high yields. 1,1’-di[3-( diphenylphosphono)propyl]-2,2’-biimidazole were deoxidized by LiAlH4 to yield 1,1’-di[3-(diphenylphosphino)propyl]-2,2’-biimidazole (L3). 1,1’-di[3-( Phosphorodithioic)propyl]-2,2’-biimidazole(L4) was efficiently synthesized by Sulfur oxidationin of 1,1’-di[3-(diphenylphosphino)propyl]-2,2’-biimidazole in good yields.
(3) 1,1’-dibutyl-2,2’-biimidazole was synthesized by nucleophilic substitution reaction between 2,2’-biimidazole and 1-butyl iodide in high yields. Biimidazole-Phosphine salt was yielded by subsitutution reaction between 1,1’-dibutyl-2,2’-biimidazole and 3-bromine propyl diphenylphosphono in good yields.
(4) The ligands L1, L2, L3, and L4 were used in palladium-catalyzed Suzuki and Heck cross-coupling reaction, the experimental results showed that ligand L3 had excellent catalytic activity and selectivity in Suzuki reaction and Heck reaction, ligand L1 showed moderate activity in Suzuki reaction, while the poor catalytic activity in Heck reaction. Ligand L4 provied to be a highly effective catalyst in Suzuki reaction, while ligand L2 was not good catalyst for Suzuki reaction. Ligands L2 and L4 ligands were unsuccessful under a very general Heck coupling system.
(1)从联咪唑出发,与3-溴丙基二苯基膦酸酯发生亲核取代反应生成1-丙基二苯基氧膦-2,2’-联咪唑,1-丙基二苯基氧膦-2,2’-联咪唑经过氢化铝锂还原反应生成配体L1——1-丙基二苯基氧膦-2,2’-联咪唑,1-丙基二苯基膦-2,2’-联咪唑经硫氧化生成配体L2——1-丙基二苯基硫膦-2,2’-联咪唑。
(2)从联咪唑出发,与3-溴丙基二苯基膦酸酯发生亲核取代反应生成1,1’-二(丙基二苯基氧膦)-2,2’联咪唑,1,1’-二(丙基二苯基氧膦)-2,2’联咪唑经过氢化铝锂还原反应生成配体L3——1,1’-二(丙基二苯基膦)-2,2’联咪唑经硫氧化生成配体L4——1,1’-二(丙基二苯基硫膦)-2,2’联咪唑。
(3)从联咪唑出发,与碘代正丁烷发生亲核取代反应生成1,1’-二丁基-2,2’联咪唑,1,1’-二丁基-2,2’联咪唑经过3-溴丙基二苯基膦酸酯取代反应生成离子液体联咪唑氧膦。
(4)把配体L1,L2,L3,L4分别应用在催化Suzuki反应和Heck反应中,实验结果表明,配体L3在催化Suzuki反应和Heck反应中都具有优越的催化活性和选择性,配体L1在催化Suzuki反应中表现出中等活性,而催化Heck反应活性较差,配体L4在催化碘代芳烃的Suzuki反应中能得到较高的产率。但配体L2催化Suzuki反应的产率则很低,配体L2和配体L4几乎都不能有效的催化Heck反应。
Transition metal-mediated cross-coupling reactions are one of the most efficient methods for the construction of C(aryl)-C(aryl), C(aryl)-N,C(aryl)-Obonds and have found widespread use in organic synthesis. Its importance in organic synthesis is evident from its application in a number of areas, ranging from natural product synthesis to materials chemistry. The development of phosphane ligands has had a huge impact in transition-metal-catalyzed reactions. Much recent work has been directed toward the development of new catalyst systems that efficiently process challenging substrates. In this paper, synthesis of functionalized phosphine ligands and their application to cross-coupling reactions have been studied.
(1) 1- 3-( diphenylphosphono)propyl-2,2’-biimidazole was synthesized by nucleophilic substitution reaction between 2,2’-biimidazole and 3-bromine propyl diphenylphosphono in high yields. 1- 3-( diphenylphosphono)propyl-2,2’-biimidazole were deoxidized by LiAlH4 to yield 1,1’-di[3-(diphenylphosphino)propyl]-2,2’-biimidazole(L1) . 1- 3-( Phosphorodithioic)propyl-2,2’-biimidazole(L2) was efficiently synthesized by Sulfur oxidationin of 1,1’-di[3-(diphenylphosphino)propyl]-2,2’-biimidazole in good yields.
(2) 1,1’-di[3-( diphenylphosphono)propyl]-2,2’-biimidazole was synthesized by nucleophilic substitution reaction between 2,2’-biimidazole and 3-bromine propyl diphenylphosphono in high yields. 1,1’-di[3-( diphenylphosphono)propyl]-2,2’-biimidazole were deoxidized by LiAlH4 to yield 1,1’-di[3-(diphenylphosphino)propyl]-2,2’-biimidazole (L3). 1,1’-di[3-( Phosphorodithioic)propyl]-2,2’-biimidazole(L4) was efficiently synthesized by Sulfur oxidationin of 1,1’-di[3-(diphenylphosphino)propyl]-2,2’-biimidazole in good yields.
(3) 1,1’-dibutyl-2,2’-biimidazole was synthesized by nucleophilic substitution reaction between 2,2’-biimidazole and 1-butyl iodide in high yields. Biimidazole-Phosphine salt was yielded by subsitutution reaction between 1,1’-dibutyl-2,2’-biimidazole and 3-bromine propyl diphenylphosphono in good yields.
(4) The ligands L1, L2, L3, and L4 were used in palladium-catalyzed Suzuki and Heck cross-coupling reaction, the experimental results showed that ligand L3 had excellent catalytic activity and selectivity in Suzuki reaction and Heck reaction, ligand L1 showed moderate activity in Suzuki reaction, while the poor catalytic activity in Heck reaction. Ligand L4 provied to be a highly effective catalyst in Suzuki reaction, while ligand L2 was not good catalyst for Suzuki reaction. Ligands L2 and L4 ligands were unsuccessful under a very general Heck coupling system.
引文
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