芳炔参与的有机反应研究
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摘要
芳炔是一类重要的有机合成中间体,广泛用于天然产物、生物碱和功能材料分子等的合成。然而,由于制备芳炔的传统方法反应条件苛刻,使其应用受到很大的限制。近年来,随着温和条件下芳炔制备新方法的发现,芳炔化学得到了巨大的发展。芳炔的反应主要包括环加成反应、亲核加成反应和过渡金属催化的反应。本论文以芳炔为反应组分,重点研究了芳炔参与的多组分环加成反应和过渡金属催化的芳炔反应,内容包括:
1.芳炔与取代昧唑的串联Diels-Alder反应
研究了芳炔与取代咪唑衍生物合成9-氨基蒽衍生物的反应。反应能在50℃条件下反应12 h以中等收率得到目标产物,研究发现反应底物的当量之比控制了反应的化学选择性,对各种单取代和双取代的咪唑衍生物都能顺利进行。机理研究发现反应历程经过了一种串联的Diels-Alder反应-逆Diels-Alder反应-Diels-Alder反应序列,反应产物有望在荧光材料领域获得应用。
2.钯催化的芳炔碳钯化-碳氢活化反应
将芳炔的碳钯化反应与杂环(吲哚)上的碳氢活化反应串联起来,发展了一种钯催化的芳炔参与的高效合成苯并菲啶类杂环的新方法。反应能在零价钯和双齿膦配体(dppp)催化下以甲苯和乙腈等体积混合溶剂中110℃回流12 h,高产率地得到产物,且对各种取代吲哚杂环具有良好的广适性。两种可能的反应机理被提出,对反应的电子效应具有一定的解释作用。测定产物的紫外—可见吸收和荧光性质,结果表明各种取代的产物具有较好的荧光性质。
3.芳炔、α-溴代苯乙酮和吡啶的三组分反应
报道了一种温和条件下的芳炔、α-溴代苯乙酮和吡啶参与的合成吡啶[2,1-a]异吲哚结构的三组分反应,通过单晶衍射确定了产物的确切结构,优化了反应条件,并在最优条件下扩展了各种取代的α-溴代苯乙酮和吡啶,探讨了底物电子效应对反应的影响。结果显示,反应只要在80℃条件下反应2h,即能以中等产物得到各种取代的吡啶[2,1-a]异吲哚结构产物。反应可能是通过α-溴代苯乙酮与吡啶原位生成1,3-偶极子进而与芳炔发生1,3-偶极环加成反应引起的。通过实验发现,产物中的吡啶[2,1-a]异吲哚结构在溶剂中存在互变异构现象,能够完全的异构为电荷分离的两可离子结构。
4.铜催化的芳炔、末端炔烃和烯丙基氯的三组分反应
首次报道了铜催化的芳炔反应。一价铜催化的末端炔烃和烯丙基氯及芳炔能有效地组装成1,6-烯炔产物。研究发现,加大烯丙基氯的量能够有效的抑制副产物的生成,碱的加入能够抑制活性中间体的质子解过程。反应对各种取代的烯丙基氯和末端炔烃都具有适用性。一种可能的机理被提出,一价铜首先与末端炔生成炔铜中间体,接着发生芳炔的碳铜化得到芳基铜,进而与烯丙基化合物氧化加成后还原消除生成了最终的1,6-烯炔类产物。
5.铜/金共催化的末端炔烃-芳炔-芳炔的串联反应
一价铜和一价金共催化的末端炔烃和芳炔反应生成2-炔基联苯类产物被报道。相同两种底物在各种催化体系如钯、铜、钯+铜及金+铜中的反应情况各不相同,其中金/铜共催化的反应首次被报道。产物对各种取代的芳炔及取代的末端炔都适用,能以较好收率得到目标产物。一种包含芳炔—金配合物中间体的可能机理被提出。产物能够在金催化下发生分子内氢芳基化得到菲类化合物。
6.芳炔与亚甲基环丙烷的环加成反应
芳炔与亚甲基环丙烷两种活泼的反应底物能够有效地发生环加成反应生成环丙烷螺二氢菲结构的产物。反应条件非常温和,能够在室温下有效地进行。对于双芳基亚甲基环丙烷底物,与苯炔发生[4+2]环加成反应,而对于位阻较小的单芳基亚甲基环丙烷底物,发生的却是[2+2+2]环加成反应。两种可能的机理用于解释上述反应现象,苯基对碳负离子的稳定作用和苯基自身的位阻作用影响了反应的底物选择性。
7.CuI催化的嗯唑硫酮与炔溴的串联反应
CuI催化的噁唑硫酮与炔溴的一种意外的串联反应被发现,反应在140℃的二甲苯溶液中进行12h能以中等收率得到手性取代的噻唑酮产物。双胺配体和碱(无水磷酸钾)对反应具有重要作用。反应对各种脂肪的和芳香的炔溴具有广泛性,各种取代的噁唑硫酮也能平稳地参与反应。通过单晶衍射发现,产物是具有构型保持的旋光纯产物,具有一定的抑菌效果。提出了一种铜催化的可能反应机理,能有效地解释反应历程。
Arynes are important intermediates in organic synthesis,which can be widely applied in the synthese of natural products,biological alkaloids and functional materials.However,the harsh reaction conditions for their preparations partially limited their applications in the organic synthesis.More recently,following the developments of mild preparation methods of arynes,the great interest has been aroused for the studies of novel aryne reactions.
There are three main kinds of reaction patterns of arynes,namely precyclic reactions,nucleophilic additions and transition-metal catalyzed transformations.In the presenting dissertation,we investigated a variety of reactions involving arynes, which include:
1.The tandem Diels-Alder cyeloaddtions of benzynes and substituted imidazoles
A kind of reactions can be used for the preparations of 9-aminoanthracenes mediated by benzynes and substituted imidazoles will be reported in this chapter. The target products can be obtained in moderate yields when the reactions were conducted in 50℃for 12 h,and the great influence on the chemoselectivities arising from the ratio of the two rection substrates has been revealed.The tandem reaction has illustrated wide tolerance to various mono and disubstituted imidazoles. Mechanism investigation has revealed a kind of tandem Diels-Alder/retro-Diels-Alder/Diels-Alder reaction sequence to rationalize the experiment reasults,and the as-produced products have displayed great probabilities in the applications in the area of fluorescence materials.
2.Palladium-Catalyzed tandem earbopalladation/C-H activation reaction of benzynes
The combination of aryne-mediated carbopalladation and C-H activaton of indoles has developed a kind of new reaction pathway can be used for the synthesis of the skeleton of benzophenathridines.The reaction can be carried out in high yield at 110℃in refluxing equivalent ratio mixture of acetonitrile and toluene in the presence of biphosphine ligand,and can tolerance various substituted indoles.Two hypothesis mechanisms have been brought forward to rationalize the experiment results,and the UV-vis adsorbed properties as well as fluorescent properties of the products has been measured and the result demonstrates that all the products own good fluorescent performances.
3.The three-component reactions of benzyens,α-bromo-acetylbenzenes and pyridines
In this chapter,we will reported a kind of new three component reaction mediated by benzynes under mild conditions,which can deliver the structure of pyrido[2,1-a]isoindoles.The final structure of the product has been confirmed by the monocrystal diffraction,and the reaction conditions have been optimized,as well as the scope and the limitations have been investigated under the optimized conditions. A plausible mechanism has been raised,which involving the 1,3-dipolar cycloadditon pathway of benzyne and the in-situ formed 1,3-dipole booting from pyridine andα-bromo-acetylbenzene.More interestingly,the pyrido[2,1-a]isoindole structure can isomerize into the charge separated form fully in some solvents,which can severely disturb the resolution of structure of the products.
4.Copper catalyzed three component assembly of benzynes,terminal alkynes and allylic chlorides
For the first time,we report the copper-catalyzed reaction of arynes.Useful 1,6-enynes can be synthesized efficiently from benzyes,terminal alkynes and allylic chlorides through the copper catalyzed procedure.During the studies of this procedure,we find that the excess of allylic chlorides can suppress the formation of byproduct,and the addition of base can do a bigger favor to this suppression.Various allylic chloride can be used in the three component assembly,and so can various terminal alkynes.A postulated mechanism has been submitted to rationalize the reaction and can be described as below:the copper catalyst can react with the terminal alkynes to form the copper(Ⅰ)intermediated,and the following carbocupration of benzyne can deliver the arylcopper species;finally,the oxidative addition and reductive elimination sequence of allylic chlorides to the arylcopper can lead to the 1,6-enyne products.
5.The cocatalyzed tandem reactions of terminal alkyne / benzyne / benzyne by copper and gold
Gold complex has been found catalyze the benzyne tranformations in cooperation with cuprous iodide.The same two components,namly termainal alkynes and benzynes,can be transformed into different products under different catalysts such as palladium,copper and gold,and in which it is the first time to report the Au/Cu cocatalyzed reactions of benzynes to generate the alkynlated biphenyl products.The reaction has been proved to be efficient towards many terminal alkynes and benzynes,and high yields can be obtained.A kind of mechanism containing the benzyne-Au complex has been postulated.The intramolecular hydroarylation of the as-described alkynlated biphenyl produnt has also been reported.
6.The cycloaddtion reactions between benzynes and methylenecyclopropanes
The two reactive intermediates,namely arynes and methylenecyclopropanes, has been proved to react with each other under catalyst free conditions.The reaction can be conducted under room temperature but deliver low yields.Two types of reaction pathway can occur decided by the structure of methylenecyclopropanes.For the diaryl substituted methylenecyclopropanes,[4+2]cycloadditions will be in occurrance in contrast to the[2+2+2]cycloadditons leading by the monoaryl methylenecyclopropanes.The two different substitution-depended reaction pathway can be explained by two distinct mechanism,and the electron effect as well as the sterecally hindered effect of the second aryl group will be responsible for the reaction diversity.
7.Tandem reaction of bromoacetynes and Oxazolidine-2-thiones
The unprecedented tandem reactions of bromoacetynes and Oxazolidine-2-thiones will constitute the main content of the eighth chapter.The tandem reaction can smoothly proceed with moderate yields at 140℃in dry xylene and critically impacted by the addition of diamine ligand.Wide substrate scope not only to bromoacetynes but also Oxazolidine-2-thiones has been illustrated.The precise structure of the product was confirmed by the ORTEP analysis and proved the reaction to be completely configuration retained pattern.The physiological activation analysis has revealed that these products possess some bacterium-inhibition effect to some extent.
1.芳炔与取代昧唑的串联Diels-Alder反应
研究了芳炔与取代咪唑衍生物合成9-氨基蒽衍生物的反应。反应能在50℃条件下反应12 h以中等收率得到目标产物,研究发现反应底物的当量之比控制了反应的化学选择性,对各种单取代和双取代的咪唑衍生物都能顺利进行。机理研究发现反应历程经过了一种串联的Diels-Alder反应-逆Diels-Alder反应-Diels-Alder反应序列,反应产物有望在荧光材料领域获得应用。
2.钯催化的芳炔碳钯化-碳氢活化反应
将芳炔的碳钯化反应与杂环(吲哚)上的碳氢活化反应串联起来,发展了一种钯催化的芳炔参与的高效合成苯并菲啶类杂环的新方法。反应能在零价钯和双齿膦配体(dppp)催化下以甲苯和乙腈等体积混合溶剂中110℃回流12 h,高产率地得到产物,且对各种取代吲哚杂环具有良好的广适性。两种可能的反应机理被提出,对反应的电子效应具有一定的解释作用。测定产物的紫外—可见吸收和荧光性质,结果表明各种取代的产物具有较好的荧光性质。
3.芳炔、α-溴代苯乙酮和吡啶的三组分反应
报道了一种温和条件下的芳炔、α-溴代苯乙酮和吡啶参与的合成吡啶[2,1-a]异吲哚结构的三组分反应,通过单晶衍射确定了产物的确切结构,优化了反应条件,并在最优条件下扩展了各种取代的α-溴代苯乙酮和吡啶,探讨了底物电子效应对反应的影响。结果显示,反应只要在80℃条件下反应2h,即能以中等产物得到各种取代的吡啶[2,1-a]异吲哚结构产物。反应可能是通过α-溴代苯乙酮与吡啶原位生成1,3-偶极子进而与芳炔发生1,3-偶极环加成反应引起的。通过实验发现,产物中的吡啶[2,1-a]异吲哚结构在溶剂中存在互变异构现象,能够完全的异构为电荷分离的两可离子结构。
4.铜催化的芳炔、末端炔烃和烯丙基氯的三组分反应
首次报道了铜催化的芳炔反应。一价铜催化的末端炔烃和烯丙基氯及芳炔能有效地组装成1,6-烯炔产物。研究发现,加大烯丙基氯的量能够有效的抑制副产物的生成,碱的加入能够抑制活性中间体的质子解过程。反应对各种取代的烯丙基氯和末端炔烃都具有适用性。一种可能的机理被提出,一价铜首先与末端炔生成炔铜中间体,接着发生芳炔的碳铜化得到芳基铜,进而与烯丙基化合物氧化加成后还原消除生成了最终的1,6-烯炔类产物。
5.铜/金共催化的末端炔烃-芳炔-芳炔的串联反应
一价铜和一价金共催化的末端炔烃和芳炔反应生成2-炔基联苯类产物被报道。相同两种底物在各种催化体系如钯、铜、钯+铜及金+铜中的反应情况各不相同,其中金/铜共催化的反应首次被报道。产物对各种取代的芳炔及取代的末端炔都适用,能以较好收率得到目标产物。一种包含芳炔—金配合物中间体的可能机理被提出。产物能够在金催化下发生分子内氢芳基化得到菲类化合物。
6.芳炔与亚甲基环丙烷的环加成反应
芳炔与亚甲基环丙烷两种活泼的反应底物能够有效地发生环加成反应生成环丙烷螺二氢菲结构的产物。反应条件非常温和,能够在室温下有效地进行。对于双芳基亚甲基环丙烷底物,与苯炔发生[4+2]环加成反应,而对于位阻较小的单芳基亚甲基环丙烷底物,发生的却是[2+2+2]环加成反应。两种可能的机理用于解释上述反应现象,苯基对碳负离子的稳定作用和苯基自身的位阻作用影响了反应的底物选择性。
7.CuI催化的嗯唑硫酮与炔溴的串联反应
CuI催化的噁唑硫酮与炔溴的一种意外的串联反应被发现,反应在140℃的二甲苯溶液中进行12h能以中等收率得到手性取代的噻唑酮产物。双胺配体和碱(无水磷酸钾)对反应具有重要作用。反应对各种脂肪的和芳香的炔溴具有广泛性,各种取代的噁唑硫酮也能平稳地参与反应。通过单晶衍射发现,产物是具有构型保持的旋光纯产物,具有一定的抑菌效果。提出了一种铜催化的可能反应机理,能有效地解释反应历程。
Arynes are important intermediates in organic synthesis,which can be widely applied in the synthese of natural products,biological alkaloids and functional materials.However,the harsh reaction conditions for their preparations partially limited their applications in the organic synthesis.More recently,following the developments of mild preparation methods of arynes,the great interest has been aroused for the studies of novel aryne reactions.
There are three main kinds of reaction patterns of arynes,namely precyclic reactions,nucleophilic additions and transition-metal catalyzed transformations.In the presenting dissertation,we investigated a variety of reactions involving arynes, which include:
1.The tandem Diels-Alder cyeloaddtions of benzynes and substituted imidazoles
A kind of reactions can be used for the preparations of 9-aminoanthracenes mediated by benzynes and substituted imidazoles will be reported in this chapter. The target products can be obtained in moderate yields when the reactions were conducted in 50℃for 12 h,and the great influence on the chemoselectivities arising from the ratio of the two rection substrates has been revealed.The tandem reaction has illustrated wide tolerance to various mono and disubstituted imidazoles. Mechanism investigation has revealed a kind of tandem Diels-Alder/retro-Diels-Alder/Diels-Alder reaction sequence to rationalize the experiment reasults,and the as-produced products have displayed great probabilities in the applications in the area of fluorescence materials.
2.Palladium-Catalyzed tandem earbopalladation/C-H activation reaction of benzynes
The combination of aryne-mediated carbopalladation and C-H activaton of indoles has developed a kind of new reaction pathway can be used for the synthesis of the skeleton of benzophenathridines.The reaction can be carried out in high yield at 110℃in refluxing equivalent ratio mixture of acetonitrile and toluene in the presence of biphosphine ligand,and can tolerance various substituted indoles.Two hypothesis mechanisms have been brought forward to rationalize the experiment results,and the UV-vis adsorbed properties as well as fluorescent properties of the products has been measured and the result demonstrates that all the products own good fluorescent performances.
3.The three-component reactions of benzyens,α-bromo-acetylbenzenes and pyridines
In this chapter,we will reported a kind of new three component reaction mediated by benzynes under mild conditions,which can deliver the structure of pyrido[2,1-a]isoindoles.The final structure of the product has been confirmed by the monocrystal diffraction,and the reaction conditions have been optimized,as well as the scope and the limitations have been investigated under the optimized conditions. A plausible mechanism has been raised,which involving the 1,3-dipolar cycloadditon pathway of benzyne and the in-situ formed 1,3-dipole booting from pyridine andα-bromo-acetylbenzene.More interestingly,the pyrido[2,1-a]isoindole structure can isomerize into the charge separated form fully in some solvents,which can severely disturb the resolution of structure of the products.
4.Copper catalyzed three component assembly of benzynes,terminal alkynes and allylic chlorides
For the first time,we report the copper-catalyzed reaction of arynes.Useful 1,6-enynes can be synthesized efficiently from benzyes,terminal alkynes and allylic chlorides through the copper catalyzed procedure.During the studies of this procedure,we find that the excess of allylic chlorides can suppress the formation of byproduct,and the addition of base can do a bigger favor to this suppression.Various allylic chloride can be used in the three component assembly,and so can various terminal alkynes.A postulated mechanism has been submitted to rationalize the reaction and can be described as below:the copper catalyst can react with the terminal alkynes to form the copper(Ⅰ)intermediated,and the following carbocupration of benzyne can deliver the arylcopper species;finally,the oxidative addition and reductive elimination sequence of allylic chlorides to the arylcopper can lead to the 1,6-enyne products.
5.The cocatalyzed tandem reactions of terminal alkyne / benzyne / benzyne by copper and gold
Gold complex has been found catalyze the benzyne tranformations in cooperation with cuprous iodide.The same two components,namly termainal alkynes and benzynes,can be transformed into different products under different catalysts such as palladium,copper and gold,and in which it is the first time to report the Au/Cu cocatalyzed reactions of benzynes to generate the alkynlated biphenyl products.The reaction has been proved to be efficient towards many terminal alkynes and benzynes,and high yields can be obtained.A kind of mechanism containing the benzyne-Au complex has been postulated.The intramolecular hydroarylation of the as-described alkynlated biphenyl produnt has also been reported.
6.The cycloaddtion reactions between benzynes and methylenecyclopropanes
The two reactive intermediates,namely arynes and methylenecyclopropanes, has been proved to react with each other under catalyst free conditions.The reaction can be conducted under room temperature but deliver low yields.Two types of reaction pathway can occur decided by the structure of methylenecyclopropanes.For the diaryl substituted methylenecyclopropanes,[4+2]cycloadditions will be in occurrance in contrast to the[2+2+2]cycloadditons leading by the monoaryl methylenecyclopropanes.The two different substitution-depended reaction pathway can be explained by two distinct mechanism,and the electron effect as well as the sterecally hindered effect of the second aryl group will be responsible for the reaction diversity.
7.Tandem reaction of bromoacetynes and Oxazolidine-2-thiones
The unprecedented tandem reactions of bromoacetynes and Oxazolidine-2-thiones will constitute the main content of the eighth chapter.The tandem reaction can smoothly proceed with moderate yields at 140℃in dry xylene and critically impacted by the addition of diamine ligand.Wide substrate scope not only to bromoacetynes but also Oxazolidine-2-thiones has been illustrated.The precise structure of the product was confirmed by the ORTEP analysis and proved the reaction to be completely configuration retained pattern.The physiological activation analysis has revealed that these products possess some bacterium-inhibition effect to some extent.
引文
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