环钯化二茂铁亚胺单膦配合物在有机氟硼酸盐存在下的Suzuki偶联反应中的应用
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摘要
本文对环钯化二茂铁亚胺单膦配合物Ⅱf催化的芳杂环卤代物与烷基三氟硼酸钾的Suzuki偶联反应进行了系统的研究；以及对α-三甲基硅-N,N-二甲基甲磺酰胺与溴苯的偶联反应进行了初步探索。
1.研究了环钯化二茂铁亚胺单膦配合物Ⅱf催化的芳杂环卤代物与烷基三氟硼酸钾的Suzuki偶联反应(Scheme 1),考察了碱、溶剂、温度、底物和催化剂对反应的影响。发现以Cs2CO3(3.0 equiv)为碱,在10:1 THF/H2O混合溶剂中以3 mol % catalystⅡf为催化剂体系温度为80℃,可以有效地催化烷基三氟硼酸钾与芳杂环卤代烃的偶联反应。得到中等到好的收率的同时,该反应还具有很好的官能团兼容性。最后当改变不同类型的烷基三氟硼酸钾参与偶联反应时,仅得到中等到低的收率。
2.使用不同钯源构成的催化体系对α-三甲基硅-N,N-二甲基甲磺酰胺与溴苯的偶联反应进行了初步研究(Scheme 2)。最好的反应条件是：Pd2(dba)3·CHCl3为催化剂,Xphos为配体,活化剂为Ag2O、0.1eq的TBAF,70℃下DMF中反应12h,得到22%气相收率。
In this thesis, the application of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos) adduct of cyclopalladated ferrocenylimine complexⅡf in Suzuki reaction was studied. The construction of benzylic sulfonamides in the presence of N,N-dimethylα-trimethylsilylsulfonamide by the catalysts of various palladium sources was also studied.
1. The application of the catalystⅡf in the aminomethylation of aryl and heteroaryl halides with potassium alkyltrifluoroborates was studied. It was found that potassium N,N-dialkylaminomethyltrifluoroborates could effectively couple with aryl and heteroaryl halides in the 10:1 THF/H2O mixture at 80℃in the presence of Cs2CO3 (3.0 equiv) as the base, giving the desired compounds in 14-87% yields. A variety of potassium alkyltrifluoroborates were also examined. (Scheme 1)
2. The application of several kinds of Pd catalyst systems in the reaction of N, N-dimethyl a-trimethylsilylsulfonamide with bromobenzene was studied. Under optimized condition (catalyst:Pd2(dba)3'CHCl3; liand:Xphos; activators:Ag2O and 0.1 eq TBAF; under 70℃using DMF last 12h), the yield was 22% which was detected by GC-MS.
1.研究了环钯化二茂铁亚胺单膦配合物Ⅱf催化的芳杂环卤代物与烷基三氟硼酸钾的Suzuki偶联反应(Scheme 1),考察了碱、溶剂、温度、底物和催化剂对反应的影响。发现以Cs2CO3(3.0 equiv)为碱,在10:1 THF/H2O混合溶剂中以3 mol % catalystⅡf为催化剂体系温度为80℃,可以有效地催化烷基三氟硼酸钾与芳杂环卤代烃的偶联反应。得到中等到好的收率的同时,该反应还具有很好的官能团兼容性。最后当改变不同类型的烷基三氟硼酸钾参与偶联反应时,仅得到中等到低的收率。
2.使用不同钯源构成的催化体系对α-三甲基硅-N,N-二甲基甲磺酰胺与溴苯的偶联反应进行了初步研究(Scheme 2)。最好的反应条件是：Pd2(dba)3·CHCl3为催化剂,Xphos为配体,活化剂为Ag2O、0.1eq的TBAF,70℃下DMF中反应12h,得到22%气相收率。
In this thesis, the application of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos) adduct of cyclopalladated ferrocenylimine complexⅡf in Suzuki reaction was studied. The construction of benzylic sulfonamides in the presence of N,N-dimethylα-trimethylsilylsulfonamide by the catalysts of various palladium sources was also studied.
1. The application of the catalystⅡf in the aminomethylation of aryl and heteroaryl halides with potassium alkyltrifluoroborates was studied. It was found that potassium N,N-dialkylaminomethyltrifluoroborates could effectively couple with aryl and heteroaryl halides in the 10:1 THF/H2O mixture at 80℃in the presence of Cs2CO3 (3.0 equiv) as the base, giving the desired compounds in 14-87% yields. A variety of potassium alkyltrifluoroborates were also examined. (Scheme 1)
2. The application of several kinds of Pd catalyst systems in the reaction of N, N-dimethyl a-trimethylsilylsulfonamide with bromobenzene was studied. Under optimized condition (catalyst:Pd2(dba)3'CHCl3; liand:Xphos; activators:Ag2O and 0.1 eq TBAF; under 70℃using DMF last 12h), the yield was 22% which was detected by GC-MS.
引文
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