磺酸酯参与的若干交叉偶联反应研究及其在类天然小分子合成中的应用
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摘要
过渡金属催化的交叉偶联反应是形成碳-碳键、碳-杂键等化学键最重要的方法之一。该方法通常以卤化物和三氟甲磺酸酯作为亲电试剂,和各种有机金属试剂在过渡金属催化剂的作用下发生偶联。经过三十多年的发展,过渡金属催化的交叉偶联反应已经被广泛应用于天然产物和药物合成,功能材料的制备等领域。
近年来,芳基磺酸酯和甲磺酸酯参与的交叉偶联反应日益受到关注。和传统的亲电试剂相比,这类化合物易于合成,比较稳定,操作简便,成本低廉,底物范围也较广。另一方面,由于不易活化,实现这类化合物的转化具有很大的创新意义,也是对有机化学家的很大挑战。
本论文的主要研究目标是发展芳基磺酸酯和甲磺酸酯参与的新型交叉偶联反应方法学,并将这些方法用于合成结构多样的具有生物活性的类天然小分子化合物。全文分为五部分,各部分内容如下:
第一部分:前言。主要综述了过渡金属催化的芳基磺酸酯和甲磺酸酯参与的交叉偶联反应的研究进展,并介绍了类天然小分子化合物合成以及若干具有生物活性的天然产物骨架。
第二部分:反应方法学研究。主要研究了芳基磺酸酯或甲磺酸酯在不同过渡金属催化下与有机硼试剂、有机硅试剂形成联二芳烃的交叉偶联反应。
1.研究了对甲苯磺酸芳基酯与芳基氟硼酸钾的Suzuki交叉偶联反应。选择合适的大体积、富电子有机膦配体,带有吸电子基团或给电子基团的对甲苯磺酸芳基酯都可以发生高效的反应。研究结果表明该反应体系的官能团兼容性也较好。
2.成功实现了铑/氮杂环卡宾催化的芳基磺酸芳基酯与芳基硼酸的交叉偶联反应。在对多种配体进行系统筛选后,我们发现氮杂环卡宾优于有机膦配体。该反应体系的成功不仅表明了铑金属催化交叉偶联反应的显著效用,也是对现有的基于有机膦配体的钯、镍催化体系的有益补充。
3.率先报道了首例钯催化的芳基磺酸芳基酯和甲磺酸酯与芳基硅烷的Hiyama交叉偶联反应。该反应体系大为拓展了此类反应亲电试剂的范围。醋酸钯和XPhos所组成的催化体系,在TBAF的存在下,可以促使多种芳基磺酸芳基酯以及甲磺酸芳基酯与不同芳基硅烷发生高效反应,生成预期的交叉偶联产物。这一崭新的反应方法对过渡金属催化的交叉偶联反应研究具有重大意义。
第三部分:反应方法学合成应用。利用上述发展的反应方法对若干天然产物骨架进行衍生修饰,合成了一系列类天然小分子化合物。
1.应用Pd(PPh_3)_4催化的对甲苯磺酸烯基酯与芳基氟硼酸钾的Suzuki交叉偶联反应合成了多个4-芳基香豆素和喹啉酮类化合物。该方法结合了对甲苯磺酸酯和氟硼酸钾各自的优势,不仅底物适用性较广,而且反应条件温和。
2.应用铑催化的对甲苯磺酸烯基酯与芳基硼酸或芳基氟硼酸钾Suzuki交叉偶联反应合成了一系列类天然小分子化合物,包括:4-芳基香豆素,喹啉酮,呋喃酮和吡咯酮类化合物。报道了第一例铑催化的对甲苯磺酸酯和芳基氟硼酸钾之间的交叉偶联反应,进一步扩大了铑催化Suzuki反应的有机金属试剂的范围。
3.发展了一种位点选择性可控的双偶联反应策略。这一崭新的策略为精确合成多样化的3,4-二取代香豆素,特别是不对称的3,4-二取代香豆素提供了一个简便的方法。南于该方法可以串联不同的化学转化,所以对于通过多种反应生成多样化的类天然小分子化合物具有重大意义。
第四部分:多取代喹啉化合物的合成。鉴于喹啉化合物显著的生物活性,我们还发展了以FeCl_3或Mg(ClO_4)_2为催化剂的温和、简便、高效的多取代喹啉合成方法。我们还进一步应用Lewis酸-表面活性剂组合催化剂实现了水相中Friedl(a|¨)nder关环反应。该反应体系为合成多取代喹啉化合物提供了一条优势明显的路线:不需要有害酸、碱以及苛刻的反应条件,而且在温和条件下应用很少量的催化剂都可以得到优秀的反应产率。因为反应在水相中进行,所以对环境友好,实验操作简便。
第五部分:实验部分。实验操作及产物表征。
在获得上述结构多样的类天然小分子化合物后,通过特定生物活性筛选测试(国家新药筛选中心),我们发现了一个良好的PTP1B抑制剂,IC_(50)值为4.65μM。对该化合物的结构优化工作正在进行中。
Transition metal-catalyzed cross-coupling reaction is one of the most important methods for the construction of C-C or C-heteroatom bonds.Aryl halides and triflates are common electrophiles for this kind of transformations.Over the past three decades, transition metal-catalyzed cross-coupling reaction has been widely used for the synthesis of natural products,pharmaceuticals and advanced materials.
However,aryl arenesulfonates and mesylates are attracting more interesting.They can be easily prepared from cheap,readily available starting materials and are less expensive,more stable,and easier to handle than the corresponding triflates. Moreover,they have a wider substrate scope than aryl halides.On the other hand, their relative inactivity appears to be a great challenge to organic chemists.
Thus,the main target of this dissertation is:methodology development of cross-coupling reactions of aryl arenesulfonates and mesylates and their applications for the synthesis of natural product-like compounds.The details of the five sections of this dissertation are as the following:
Section 1:Review of the development of transition metal-catalyzed cross-coupling reaction of aryl arenesulfonates and mesylates,and introduction of natural product-like small molecules and several natural product structures with remarkable biological properties.
Section 2:Studies of transition metal-catalyzed cross-couplings of aryl arenesulfonates or mesylates with organoboron compounds,aryl silanes.
1.Investigated the Suzuki cross-coupling reaction of aryl tosylates with potassium aryl trifluoroborates.Both aryl tosylates with electron-donating group and aryl arenesulfonates with electron-withdrawing group coupled efficiently with various potassium aryl trifluoroborates by using a bulky electron-rich phosphine ligand. This reaction also shows good functional group tolerance.
2.Realized Rh/NHC catalyzed cross-coupling reaction of aryl arenesulfonates with arylboronic acids.NHC ligand was found to be more efficient than phosphine ligand in this reaction.The results not only demonstrate the efficiency of the Rh catalyst in cross-couplings of aryl arenesulfonates,but also provide an interesting complement to the phosphine-based palladium or nickel catalyst systems.
3.Reported the first example of Pd-catalyzed Hiyama reaction of aryl arenesulfonates or mesylates with aryl silanes.In the presence of TBAF,various aryl arenesulfonates and mesylates were transformed into the desired cross-coupling products.This method broadened the scope of electrophiles of Hiyama reaction significantly.
Section 3:Synthesis of a series of natural product-like small molecules utilizing the reaction methods developed in Section 2.
1.Synthesized 4-aryl coumarins and quinolin-2(1H)-ones via Pd-catalyzed Suzuki reaction of alkenyl tosylates with potassium aryl trifluoroborates.This method benefits from the attractive features and advantages of both substrates and shows good functional group tolerance.
2.Synthesized a series of natural product-like small molecules(4-aryl coumarins, quinolin-2(1H)-ones,pyrones,and furan-2(5H)-ones) via Rh-catalyzed reaction of alkenyl tosylates with arylboronic acids or potassium aryl trifluoroborates.
3.Developed a site-selective cross-coupling strategy for the concise synthesis of 3,4-disubstituted coumarins.This work opens the door for numerous synthetic applications to diversified structures.
Section 4:Considering the remarkable biological properties of quinoline structure, we have developed an efficient and mild route for the access of quinolines utilizing FeCl_3 or Mg(ClO_4)_2 as a novel catalyst via Friedl(?)nder annulation.We also realized this transformation in water by using Lewis acid-surfactant-combined catalyst. Various polysubstituted and polycyclic quinolines were obtained in excellent yields.
Section 5:Experiment procedure and characterization.
Collaborated with biologists(National Center for Drug Screening),we have screened these natural product-like small molecules in properly selected biological assays.Encouraging,a small molecule inhibitor of PTP1B was discovered with an IC_(50) value of 4.65μM.Further investigation is underway.
近年来,芳基磺酸酯和甲磺酸酯参与的交叉偶联反应日益受到关注。和传统的亲电试剂相比,这类化合物易于合成,比较稳定,操作简便,成本低廉,底物范围也较广。另一方面,由于不易活化,实现这类化合物的转化具有很大的创新意义,也是对有机化学家的很大挑战。
本论文的主要研究目标是发展芳基磺酸酯和甲磺酸酯参与的新型交叉偶联反应方法学,并将这些方法用于合成结构多样的具有生物活性的类天然小分子化合物。全文分为五部分,各部分内容如下:
第一部分:前言。主要综述了过渡金属催化的芳基磺酸酯和甲磺酸酯参与的交叉偶联反应的研究进展,并介绍了类天然小分子化合物合成以及若干具有生物活性的天然产物骨架。
第二部分:反应方法学研究。主要研究了芳基磺酸酯或甲磺酸酯在不同过渡金属催化下与有机硼试剂、有机硅试剂形成联二芳烃的交叉偶联反应。
1.研究了对甲苯磺酸芳基酯与芳基氟硼酸钾的Suzuki交叉偶联反应。选择合适的大体积、富电子有机膦配体,带有吸电子基团或给电子基团的对甲苯磺酸芳基酯都可以发生高效的反应。研究结果表明该反应体系的官能团兼容性也较好。
2.成功实现了铑/氮杂环卡宾催化的芳基磺酸芳基酯与芳基硼酸的交叉偶联反应。在对多种配体进行系统筛选后,我们发现氮杂环卡宾优于有机膦配体。该反应体系的成功不仅表明了铑金属催化交叉偶联反应的显著效用,也是对现有的基于有机膦配体的钯、镍催化体系的有益补充。
3.率先报道了首例钯催化的芳基磺酸芳基酯和甲磺酸酯与芳基硅烷的Hiyama交叉偶联反应。该反应体系大为拓展了此类反应亲电试剂的范围。醋酸钯和XPhos所组成的催化体系,在TBAF的存在下,可以促使多种芳基磺酸芳基酯以及甲磺酸芳基酯与不同芳基硅烷发生高效反应,生成预期的交叉偶联产物。这一崭新的反应方法对过渡金属催化的交叉偶联反应研究具有重大意义。
第三部分:反应方法学合成应用。利用上述发展的反应方法对若干天然产物骨架进行衍生修饰,合成了一系列类天然小分子化合物。
1.应用Pd(PPh_3)_4催化的对甲苯磺酸烯基酯与芳基氟硼酸钾的Suzuki交叉偶联反应合成了多个4-芳基香豆素和喹啉酮类化合物。该方法结合了对甲苯磺酸酯和氟硼酸钾各自的优势,不仅底物适用性较广,而且反应条件温和。
2.应用铑催化的对甲苯磺酸烯基酯与芳基硼酸或芳基氟硼酸钾Suzuki交叉偶联反应合成了一系列类天然小分子化合物,包括:4-芳基香豆素,喹啉酮,呋喃酮和吡咯酮类化合物。报道了第一例铑催化的对甲苯磺酸酯和芳基氟硼酸钾之间的交叉偶联反应,进一步扩大了铑催化Suzuki反应的有机金属试剂的范围。
3.发展了一种位点选择性可控的双偶联反应策略。这一崭新的策略为精确合成多样化的3,4-二取代香豆素,特别是不对称的3,4-二取代香豆素提供了一个简便的方法。南于该方法可以串联不同的化学转化,所以对于通过多种反应生成多样化的类天然小分子化合物具有重大意义。
第四部分:多取代喹啉化合物的合成。鉴于喹啉化合物显著的生物活性,我们还发展了以FeCl_3或Mg(ClO_4)_2为催化剂的温和、简便、高效的多取代喹啉合成方法。我们还进一步应用Lewis酸-表面活性剂组合催化剂实现了水相中Friedl(a|¨)nder关环反应。该反应体系为合成多取代喹啉化合物提供了一条优势明显的路线:不需要有害酸、碱以及苛刻的反应条件,而且在温和条件下应用很少量的催化剂都可以得到优秀的反应产率。因为反应在水相中进行,所以对环境友好,实验操作简便。
第五部分:实验部分。实验操作及产物表征。
在获得上述结构多样的类天然小分子化合物后,通过特定生物活性筛选测试(国家新药筛选中心),我们发现了一个良好的PTP1B抑制剂,IC_(50)值为4.65μM。对该化合物的结构优化工作正在进行中。
Transition metal-catalyzed cross-coupling reaction is one of the most important methods for the construction of C-C or C-heteroatom bonds.Aryl halides and triflates are common electrophiles for this kind of transformations.Over the past three decades, transition metal-catalyzed cross-coupling reaction has been widely used for the synthesis of natural products,pharmaceuticals and advanced materials.
However,aryl arenesulfonates and mesylates are attracting more interesting.They can be easily prepared from cheap,readily available starting materials and are less expensive,more stable,and easier to handle than the corresponding triflates. Moreover,they have a wider substrate scope than aryl halides.On the other hand, their relative inactivity appears to be a great challenge to organic chemists.
Thus,the main target of this dissertation is:methodology development of cross-coupling reactions of aryl arenesulfonates and mesylates and their applications for the synthesis of natural product-like compounds.The details of the five sections of this dissertation are as the following:
Section 1:Review of the development of transition metal-catalyzed cross-coupling reaction of aryl arenesulfonates and mesylates,and introduction of natural product-like small molecules and several natural product structures with remarkable biological properties.
Section 2:Studies of transition metal-catalyzed cross-couplings of aryl arenesulfonates or mesylates with organoboron compounds,aryl silanes.
1.Investigated the Suzuki cross-coupling reaction of aryl tosylates with potassium aryl trifluoroborates.Both aryl tosylates with electron-donating group and aryl arenesulfonates with electron-withdrawing group coupled efficiently with various potassium aryl trifluoroborates by using a bulky electron-rich phosphine ligand. This reaction also shows good functional group tolerance.
2.Realized Rh/NHC catalyzed cross-coupling reaction of aryl arenesulfonates with arylboronic acids.NHC ligand was found to be more efficient than phosphine ligand in this reaction.The results not only demonstrate the efficiency of the Rh catalyst in cross-couplings of aryl arenesulfonates,but also provide an interesting complement to the phosphine-based palladium or nickel catalyst systems.
3.Reported the first example of Pd-catalyzed Hiyama reaction of aryl arenesulfonates or mesylates with aryl silanes.In the presence of TBAF,various aryl arenesulfonates and mesylates were transformed into the desired cross-coupling products.This method broadened the scope of electrophiles of Hiyama reaction significantly.
Section 3:Synthesis of a series of natural product-like small molecules utilizing the reaction methods developed in Section 2.
1.Synthesized 4-aryl coumarins and quinolin-2(1H)-ones via Pd-catalyzed Suzuki reaction of alkenyl tosylates with potassium aryl trifluoroborates.This method benefits from the attractive features and advantages of both substrates and shows good functional group tolerance.
2.Synthesized a series of natural product-like small molecules(4-aryl coumarins, quinolin-2(1H)-ones,pyrones,and furan-2(5H)-ones) via Rh-catalyzed reaction of alkenyl tosylates with arylboronic acids or potassium aryl trifluoroborates.
3.Developed a site-selective cross-coupling strategy for the concise synthesis of 3,4-disubstituted coumarins.This work opens the door for numerous synthetic applications to diversified structures.
Section 4:Considering the remarkable biological properties of quinoline structure, we have developed an efficient and mild route for the access of quinolines utilizing FeCl_3 or Mg(ClO_4)_2 as a novel catalyst via Friedl(?)nder annulation.We also realized this transformation in water by using Lewis acid-surfactant-combined catalyst. Various polysubstituted and polycyclic quinolines were obtained in excellent yields.
Section 5:Experiment procedure and characterization.
Collaborated with biologists(National Center for Drug Screening),we have screened these natural product-like small molecules in properly selected biological assays.Encouraging,a small molecule inhibitor of PTP1B was discovered with an IC_(50) value of 4.65μM.Further investigation is underway.
引文
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