几种无溶剂加成反应及烯烃卤胺化反应研究
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摘要
当代社会的高速发展需要大量的化工产品,不可避免地会产生许多环境问题.如何在环境友好的条件下进行化学合成,是化学家们当前最迫切的任务之一。在这样的背景下,一些更为安全和便捷的合成手段被开发,同时许多传统的有机溶剂和贵重并且有毒的重金属催化剂被无毒无害的溶剂和催化剂代替。其中,利用机械研磨促进的无溶剂反应和以水作为溶剂的有机反应近年来备受关注;同时用有机小分子代替金属催化的有机反应也是化学界的重要议题。本论文的主要工作包括机械研磨条件下的加成反应和烯烃卤胺化反应两个方面.具体内容如下:
1.在固相机械研磨条件下合成二氯吖丙啶化合物,并研究了它们的水解反应。芳香醛和芳香胺1∶1混合反应后,生成的亚胺未经分离,直接进行下一步反应,与在KF/Al_2O_3存在下生成的二氯卡宾作用,生成高活性的二氯吖丙啶产物。在Lewis酸的存在下,产物很容易进行水解反应,生成氯代的苯乙酰胺。整个反应在无溶剂条件下进行,而且只需要少量的卡宾源即可以很高的产率得到产物。
2.利用固相机械研磨技术,成功实现了Lewis酸催化下的吲哚对环氧化合物的开环反应。通过研究各种Lewis酸的催化作用发现,水合三氯化铟的效果最好。此反应仅限于由查儿酮衍生的环氧化合物,对于一般的环氧,效果不好。该机械研磨方法的优点是不需要使用有毒的有机溶剂,反应时间较短,反应温和,后处理简单。
3.利用高价碘化合物,在机械研磨条件下实现了缺电子烯烃的氯胺化反应。和以前的方法相比较,此反应不需要任何有机溶剂和金属催化剂,能在潮湿空气中顺利进行,反应时间短,产率和选择性非常好。醋酸碘苯这种强氧化剂首次被用来实现此类反应,并且亚催化量(50 mol%)就能使反应很好地进行。对比研究发现,在机械研磨条件下,各种金属氯化物对此反应都有一定的促进作用,其中三氯化铟的效果最好。在各种有机溶剂中,醋酸碘苯的效果非常差,完全得不到或者只能以很低的产率得到产物,充分显示了固相研磨反应的特点和优势。
4.研究了无溶剂条件下醋酸碘苯促进的溴胺化反应。在醋酸碘苯的存在下,以对甲苯磺酰胺为氮源,以NBS为溴源,成功地实现了缺电子烯烃和苯乙烯的溴胺化反应。在该反应中,醋酸碘苯也是非当量的(75 mol%),产率较高,产物的非对映选择性也非常好。
5.系统研究了有机溶剂中高价碘化合物促进的烯烃氯胺和溴胺化反应。通过对溶剂的筛选,我们发现此类型的反应只有在二氯甲烷中才能很好地进行,获得与固相条件下相似的结果.我们还进一步研究了各种高价碘化合物对该反应的影响,发现虽然这些化合物对烯烃卤胺化反应均有一定的促进作用,但是醋酸碘苯的效果是最好的。在此条件下,烯烃的溴胺化反应被成功地放大到10 g以上的规模,有力地证明了此反应的优势。同时,我们还研究了不同的氮源和卤素源对反应的影响,并对反应可能的机理进行了一些探讨。
6.首次实现了水相中质子酸促进的烯烃氯胺化反应。以前报道的此类反应,都是在有毒的有机溶剂,如乙腈中进行的,而且需要加入分子筛以除去反应体系中的水。以氯胺-T为氮氯源,在质子酸,如硫酸的存在下,缺电子烯烃很容易被氯胺化,以很高的产率和选择性获得产物。并且,这个反应能在并且只能在水中进行,在有机溶剂中我们得不到任何产物。还有一个很大的优点,就是这个反应能放大到10 g以上的量,充分展示了其可能的工业用途。
7.研究了水相条件下,醋酸碘苯催化的溴胺化反应。在纯水体系中,以对甲苯磺酰胺为氮源,以NBS为溴源,烯烃的溴胺化反应能够在20 mol%甚至更少的醋酸碘苯催化下进行。该反应效率非常高,只需要几十分钟,反应便能完成,以很高的产率和立体选择性获得产物。此研究首次实现了醋酸碘苯的催化量使用。此外,我们还发现苯乙烯的双键也能被高区域选择性地溴胺化,证明了醋酸碘苯对此类反应有良好的催化效果.
Large numbers of chemical products were required in the rapid developing modern society which can cause many serious environmental problems in the producing process.To perform the chemical synthesis in an environmentally friendly way is one of the most urgent tasks assigned to our chemists.In this situation,some safer and more convenient synthetic methods have been developed,replacing the traditional organic solvents and precious and toxic metal catalysts with environmentally safe ones.Performing organic reactions under solvent-free mechanical milling conditions,utilizing water as reaction medium,as well as the small organic molecular-catalyzed reactions are among the most concerning topics.In this thesis,investigations are focused on the mechanochemical solvent-free addition reactions and aminohalogenation reactions of olefins.
1.gern-Dichloroaziridines were synthesized in a ball mill under solvent-free conditions.Their hydrolysis promoted by Lewis acid was also investigated under the same conditions.The aniline and aromatic aldehyde were mixed in a reaction vessel,and the thus formed imine could react directly with dichlorocarbene generated from chloroform in the presence of KF/Al_2O_3.With the promotion of Lewis acid,these aziridines were readily hydrolyzed to generateα-chloro-phenyl-acetamide.This solvent-free reaction required only a small quantity of carbene source to give the final product in high yield.
2.The Friedel-Crafts type alkylation reaction of indole with epoxy ketones were carried out successfully under ball-milling conditions in the presence of Lewis acid as catalyst.Further investigation indicated that InCl_3·4H_2O afforded the highest yield.The advantage of this methodology is solventless reaction condition, short reaction time,mild reaction process and simple manipulation.
3.The aminochlorination reaction of electron-deficient olefins promoted by hypervalent iodine compound was realized under solvent-free mechanochemical conditions.Compared with the previous methods,this process could be performed in moisture without any solvent and metal catalyst,affording the products in good yields and high regio- and diastereoselectivities with shorter reaction time.The strong oxidant PhI(OAc)_2 was used to promote this reaction for the first time,and substoichiometric loading(50 mol%) was enough to give a high-yielding reaction.Under the same condition,various metal chlorides could also promote this aminochlorination reaction to some extent,among which InCl_3·4H_2O gave the best result.When the reaction was performed in organic solvents,none or only low-yielding product was obtained,which demonstrated the superiority of our ball-milling method.
4.The PhI(OAc)_2-promoted aminobromination reaction of electron-deficient olefins with sulfonamide as nitrogen source and NBS as bromine source under mechanical milling conditions was demonstrated.In this reaction, substoichiometric PhI(OAc)_2 was used and the products were obtained in good yields and high regio- and diastereoselectivities.
5.An efficient and practical procedure for the aminohalogenation of electron-deficient olefins promoted by hypervalent iodine compounds has been demonstrated.The catalytic efficiency of various hypervalent iodine compounds with different carboxylic and sulfonic ligands has also been investigated and (diacetoxyiodo)benzene exhibited the highest activity.The aminobromination reaction could be performed on multi-gram scale which exhibited the advantage of this reaction.Furthermore,the influence of various nitrogen and bromine sources was investigated and the possible mechanism of this reaction was discussed.
6.The aminochlorination of electron-deficient olefins was realized in water for the first time promoted by Bronsted acids.Previously,these reactions were performed in dry acetonitrile which was manipulatively complex and environmentally unfriendly.In this study,we found that the electron-deficient olefins could be easily aminochlorinated with high yield and selectivity in acidic water with Chloramine-T as chlorine and nitrogen source.This reaction could only be performed in water;when organic solvent was used,the reaction failed. Furthermore,the reaction could proceed successfully on multi-gram scale,which exhibited the possible application in industry.
7.With TsNH_2 and NBS as nitrogen and bromine sources respectively,the aminobromination reaction of electron-deficient olefms could be catalyzed by 20 mol%of(diacetoxyiodo)benzene,and the reaction could only proceed in pure water.This reaction was performed with high efficiency and stereoselectivity. Furthermore,the double bond of styrene was also tolerable under the present condition,which demonstrated that(diacetoxyiodo)benzene was a powerful catalyst in this kind of reaction.
1.在固相机械研磨条件下合成二氯吖丙啶化合物,并研究了它们的水解反应。芳香醛和芳香胺1∶1混合反应后,生成的亚胺未经分离,直接进行下一步反应,与在KF/Al_2O_3存在下生成的二氯卡宾作用,生成高活性的二氯吖丙啶产物。在Lewis酸的存在下,产物很容易进行水解反应,生成氯代的苯乙酰胺。整个反应在无溶剂条件下进行,而且只需要少量的卡宾源即可以很高的产率得到产物。
2.利用固相机械研磨技术,成功实现了Lewis酸催化下的吲哚对环氧化合物的开环反应。通过研究各种Lewis酸的催化作用发现,水合三氯化铟的效果最好。此反应仅限于由查儿酮衍生的环氧化合物,对于一般的环氧,效果不好。该机械研磨方法的优点是不需要使用有毒的有机溶剂,反应时间较短,反应温和,后处理简单。
3.利用高价碘化合物,在机械研磨条件下实现了缺电子烯烃的氯胺化反应。和以前的方法相比较,此反应不需要任何有机溶剂和金属催化剂,能在潮湿空气中顺利进行,反应时间短,产率和选择性非常好。醋酸碘苯这种强氧化剂首次被用来实现此类反应,并且亚催化量(50 mol%)就能使反应很好地进行。对比研究发现,在机械研磨条件下,各种金属氯化物对此反应都有一定的促进作用,其中三氯化铟的效果最好。在各种有机溶剂中,醋酸碘苯的效果非常差,完全得不到或者只能以很低的产率得到产物,充分显示了固相研磨反应的特点和优势。
4.研究了无溶剂条件下醋酸碘苯促进的溴胺化反应。在醋酸碘苯的存在下,以对甲苯磺酰胺为氮源,以NBS为溴源,成功地实现了缺电子烯烃和苯乙烯的溴胺化反应。在该反应中,醋酸碘苯也是非当量的(75 mol%),产率较高,产物的非对映选择性也非常好。
5.系统研究了有机溶剂中高价碘化合物促进的烯烃氯胺和溴胺化反应。通过对溶剂的筛选,我们发现此类型的反应只有在二氯甲烷中才能很好地进行,获得与固相条件下相似的结果.我们还进一步研究了各种高价碘化合物对该反应的影响,发现虽然这些化合物对烯烃卤胺化反应均有一定的促进作用,但是醋酸碘苯的效果是最好的。在此条件下,烯烃的溴胺化反应被成功地放大到10 g以上的规模,有力地证明了此反应的优势。同时,我们还研究了不同的氮源和卤素源对反应的影响,并对反应可能的机理进行了一些探讨。
6.首次实现了水相中质子酸促进的烯烃氯胺化反应。以前报道的此类反应,都是在有毒的有机溶剂,如乙腈中进行的,而且需要加入分子筛以除去反应体系中的水。以氯胺-T为氮氯源,在质子酸,如硫酸的存在下,缺电子烯烃很容易被氯胺化,以很高的产率和选择性获得产物。并且,这个反应能在并且只能在水中进行,在有机溶剂中我们得不到任何产物。还有一个很大的优点,就是这个反应能放大到10 g以上的量,充分展示了其可能的工业用途。
7.研究了水相条件下,醋酸碘苯催化的溴胺化反应。在纯水体系中,以对甲苯磺酰胺为氮源,以NBS为溴源,烯烃的溴胺化反应能够在20 mol%甚至更少的醋酸碘苯催化下进行。该反应效率非常高,只需要几十分钟,反应便能完成,以很高的产率和立体选择性获得产物。此研究首次实现了醋酸碘苯的催化量使用。此外,我们还发现苯乙烯的双键也能被高区域选择性地溴胺化,证明了醋酸碘苯对此类反应有良好的催化效果.
Large numbers of chemical products were required in the rapid developing modern society which can cause many serious environmental problems in the producing process.To perform the chemical synthesis in an environmentally friendly way is one of the most urgent tasks assigned to our chemists.In this situation,some safer and more convenient synthetic methods have been developed,replacing the traditional organic solvents and precious and toxic metal catalysts with environmentally safe ones.Performing organic reactions under solvent-free mechanical milling conditions,utilizing water as reaction medium,as well as the small organic molecular-catalyzed reactions are among the most concerning topics.In this thesis,investigations are focused on the mechanochemical solvent-free addition reactions and aminohalogenation reactions of olefins.
1.gern-Dichloroaziridines were synthesized in a ball mill under solvent-free conditions.Their hydrolysis promoted by Lewis acid was also investigated under the same conditions.The aniline and aromatic aldehyde were mixed in a reaction vessel,and the thus formed imine could react directly with dichlorocarbene generated from chloroform in the presence of KF/Al_2O_3.With the promotion of Lewis acid,these aziridines were readily hydrolyzed to generateα-chloro-phenyl-acetamide.This solvent-free reaction required only a small quantity of carbene source to give the final product in high yield.
2.The Friedel-Crafts type alkylation reaction of indole with epoxy ketones were carried out successfully under ball-milling conditions in the presence of Lewis acid as catalyst.Further investigation indicated that InCl_3·4H_2O afforded the highest yield.The advantage of this methodology is solventless reaction condition, short reaction time,mild reaction process and simple manipulation.
3.The aminochlorination reaction of electron-deficient olefins promoted by hypervalent iodine compound was realized under solvent-free mechanochemical conditions.Compared with the previous methods,this process could be performed in moisture without any solvent and metal catalyst,affording the products in good yields and high regio- and diastereoselectivities with shorter reaction time.The strong oxidant PhI(OAc)_2 was used to promote this reaction for the first time,and substoichiometric loading(50 mol%) was enough to give a high-yielding reaction.Under the same condition,various metal chlorides could also promote this aminochlorination reaction to some extent,among which InCl_3·4H_2O gave the best result.When the reaction was performed in organic solvents,none or only low-yielding product was obtained,which demonstrated the superiority of our ball-milling method.
4.The PhI(OAc)_2-promoted aminobromination reaction of electron-deficient olefins with sulfonamide as nitrogen source and NBS as bromine source under mechanical milling conditions was demonstrated.In this reaction, substoichiometric PhI(OAc)_2 was used and the products were obtained in good yields and high regio- and diastereoselectivities.
5.An efficient and practical procedure for the aminohalogenation of electron-deficient olefins promoted by hypervalent iodine compounds has been demonstrated.The catalytic efficiency of various hypervalent iodine compounds with different carboxylic and sulfonic ligands has also been investigated and (diacetoxyiodo)benzene exhibited the highest activity.The aminobromination reaction could be performed on multi-gram scale which exhibited the advantage of this reaction.Furthermore,the influence of various nitrogen and bromine sources was investigated and the possible mechanism of this reaction was discussed.
6.The aminochlorination of electron-deficient olefins was realized in water for the first time promoted by Bronsted acids.Previously,these reactions were performed in dry acetonitrile which was manipulatively complex and environmentally unfriendly.In this study,we found that the electron-deficient olefins could be easily aminochlorinated with high yield and selectivity in acidic water with Chloramine-T as chlorine and nitrogen source.This reaction could only be performed in water;when organic solvent was used,the reaction failed. Furthermore,the reaction could proceed successfully on multi-gram scale,which exhibited the possible application in industry.
7.With TsNH_2 and NBS as nitrogen and bromine sources respectively,the aminobromination reaction of electron-deficient olefms could be catalyzed by 20 mol%of(diacetoxyiodo)benzene,and the reaction could only proceed in pure water.This reaction was performed with high efficiency and stereoselectivity. Furthermore,the double bond of styrene was also tolerable under the present condition,which demonstrated that(diacetoxyiodo)benzene was a powerful catalyst in this kind of reaction.
引文
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* 6.2.3这一部分的实验工作主要由安徽建筑工业学院的夏静静博士完成,在此表示感谢。发表文章见:Xia,J.-J.;Wu,X.-L.;Wang,G.-W.ARKIVOC 2008,(ⅹⅵ),22-28.
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* 6.2.3这一部分的实验工作主要由安徽建筑工业学院的夏静静博士完成,在此表示感谢。发表文章见:Xia,J.-J.;Wu,X.-L.;Wang,G.-W.ARKIVOC 2008,(ⅹⅵ),22-28.
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