叔膦催化合成卤代联烯及其Suzuki交叉偶联反应的研究
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摘要
卤代联烯具有很高的反应活性,能发生取代、加成、偶联等多种反应,是有机合成的重要中间体,广泛应用于各类天然产物和药物分子的合成中。但目前报道的各种卤代联烯的合成方法都存在着产率低、选择性差、操作复杂、污染严重等缺点。尤其是用二氯亚砜、浓盐酸等做卤代试剂时,对环境污染更加严重。有机催化是近期发展起来的模拟酶催化,是一个热门的新领域。它效率高、选择性好、反应条件温和,用有机催化方法合成卤代联烯符合绿色化学要求,是理想的方向。
首次研究了N-卤代丁二酰亚胺(NXS)／三苯基膦体系下由炔丙基醇合成卤代联烯的反应,该反应包括卤代、氧化、异构化等过程。发现三苯基膦在其中起到了促进卤代以及脱氧的作用,通过以上研究,本文设计了叔膦／1,4苯二酚／N-卤代丁二酰亚胺这一新的有机催化卤代体系。在该催化体系中,5 mol%叔膦即可顺利催化N-氯代丁二酰亚胺(NCS)对炔丙基醇卤代,一步合成氯代联烯。该方法具有选择性好、产率良好、操作简便、环境污染小等优点。优于已有文献报道方法。
筛选了叔膦催化剂,发现三环己基膦效果最佳。三苯基膦次之,在研究机理的过程中发现它不仅是催化剂而且是脱氧剂,常见的还原剂在该反应中并不能脱除炔醇羟基中的氧,但它们能将三苯氧膦还原成三苯基膦,从而实现催化循环。多元酚是有效的还原剂,其中1,4-苯二酚(HQ)性能最佳。
在总结实验证据基础上,提出了由炔丙醇和HQ/NCS/PPh3制备氯代联烯可能的反应机理。包括三苯基膦与N-卤代丁二酰亚胺反应生成卤代三苯基膦正离子活性中间物,它对羟基实施卤代。三苯基膦脱除羟基中的氧生成三苯氧膦。1,4-苯二酚将三苯氧膦还原成三苯基膦,完成催化循环,
筛选出了无还原剂存在时的最佳反应条件：炔丙基醇(1.0 mmol)、NXS(1.55 mmol)、PPh3(1.50 mmol)、CH2Cl2(5 mL)、-15-25℃下搅拌1h。在此条件下氯代联烯的产率最高可达88%,溴代联烯的产率最高可达86%。有还原剂存在时的最佳反应条件：炔丙基醇(1.00 mmol)、NCS(1.55 mmol)、HQ(1.5 mmol)、PPh3(5 mmol%)、CH2Cl2(5 mL),室温下搅拌24 h,氯代联烯产率最高可达85%。合成的氯代联烯和溴代联烯均未见文献报道。
Suzuki交叉偶联反应是重要的现代有机合成方法。用卤代联烯Suzuki交叉偶联反应合成含联烯结构的分子为合成药物、天然化合物探讨一个新路线的工作也具有实际意义。但卤代联烯基作为Suzuki交叉偶联反应底物之前则极少有文献报导。为此,研究了溴代联烯与芳基硼酸的Suzuki交叉偶联反应。发现二-(二苯基膦乙酸)钯是芳基溴代联烯Suzuki交叉偶联反应的有效催化剂,在室温下的催化活性很高,最高产率达93%；研究二-(二苯基膦乙酸钯)催化1-溴-1-丁基-3-(4’-溴苯基)-1,2丙二烯(3c)与苯硼酸Suzuki交叉偶联反应,发现它能高选择性地催化溴代联烯上的C-Br而不是溴苯基上的C-Br参加反应。
二-(二苯基膦乙醇)-二氯合镍也能有效地催化芳基溴代联烯Suzuki交叉偶联反应。最高产率达87%。
生成的含联烯结构的交叉偶联产物均未见文献报道。
Haloallenes which has been recognized as important fundamental organic units are often used as intermediates for the preparation of natural products and pharmaceuticals due to their high reactivity in substitution, addition, coupling and other reactions. However, the reported methods for the synthesis of haloallenes have many disadvantages such as low-yield, poor selectivity, complex manipulation and serious pollution problems. Especially, dichlorosulfoxide, concentrated hydrochloric acid and other halogenated reagents have caused severe damage to the environment. Recently, the field of enzyme catalysis and organocatalysis has been rapidly developing and attracted an increasing number of research groups around the world. Chemical transformations in this field generally possess advantages such as high efficiency, good selectivity and mild conditions, thus the synthesis of halo-allenes directed by the concept of organocatalysis is according to green chemistry concepts and would be an ideal strategy.
The reaction of propargyl alcohols with N-halogenated succinimide under the NCX/PPh3 system providing chloroallenes or bromoallenes via three stages including halogenation, oxidation and isomerization was firstly studied. It is found that PPh3 not only facilitate the step of halogenation but also act as a deoxidant. Base on this result, we proposed the triphosphine/ 1,4-hydroquinone/NXS as an novel organocatalytical system for the halogenation reaction. In this catalytical system, propargyl alcohols could be halogenated by NCS in presence of only 5 mol% of triphosphine to afford chloroallenes in one step. This method possesses a series of merits containing good selectivity, high yield, simple manipulation and limited pollution which is better than reported methods.
Triphosphines was found to be catalyst in the employed systerms, and demonstrates that Cy3P is the best catalyst, PPh3 as the second one. The research on the mechanism reveals that the triphosphine acts as catalyst and deoxidant at the same time. Generally, the oxygen atom of the propargyl alcohols can not be absorbed by reductant directly. However, the deoxidant can reduce triphenylphosphine oxide to triphenylphosphine which achieves the catalytical cycles.. Polyphenols were the effective reductant and 1,4-dihydroxybenzene was the best one.
Based on the obtained results, a proposed mechanism of the halogenation of propargyl alcohols under the HQ/NCS/PPh3 system was tentatively given. In this mechanism:hydroxyl was halogenated by Cl-PPh3 cation as the active intermediate generated by the reaction of triphenylphosphine with N-halogenated succinimide. Then the oxygen atom in hydroxyl was removed by triphenylphosphine giving triphenylphosphine oxide. At last, triphenylphosphine oxide was reduced to triphenylphosphine by 1,4-dihydroxybenzene and start a new catalytical cycle.
The optimized condition in the absence of reductant:propargyl alcohol (1.0 mmol), NXS (1.55 mmol), triphenylphosphine (1.50 mmol), CH2Cl2 (5 mL) and stirred for 1 h under-15 to 25℃. Under this condition, up to 88% and 86% yields can be obtained for chloroallene and bromoallene, respectively. In the presence of reductant:propargyl alcohol (1.0 mmol), NCS (1.55 mmol), HQ (1.5 mmol), triphenylphosphine (5 mmol%), CH2Cl2 (5 mL) and stirred for 24 h under room temperature. All the chloroallenes and bromoallenes are new compounds.
Suzuki cross-coupling reaction is one of the most important methods in modern organic synthesis. An investigation of the Suzuki cross-coupling reaction of haloallenes to synthesize natural products and pharmaceuticals containing allene structure was extraordinary significance. However, up to now only a few reports could be found in this area. Thus, suzuki cross-coupling of bromoallene and arylboric acid was studied and found that di[2-(diphenylphosphino)acetic acid] palladium was an very effective catalyst, even under room temperature the yield can reach up to 93%. It was found that C-Br on bromoallene rather than on benzene ring readily took part in Suzuki cross-coupling reaction between 1-bromo-l-butyl- (4-bromophenyl)-1,2-propadiene and aryl boric acid catalyzed by di[2-(diphenylphosphino)acetic acid] palladium.
NiCl2(Ph2PCH2CH2O)2 was also found to be a effective catalyst for the Suzuki reaction and led up to 87% yield.
All cross-coupling products of bromoallene are new compounds.
首次研究了N-卤代丁二酰亚胺(NXS)／三苯基膦体系下由炔丙基醇合成卤代联烯的反应,该反应包括卤代、氧化、异构化等过程。发现三苯基膦在其中起到了促进卤代以及脱氧的作用,通过以上研究,本文设计了叔膦／1,4苯二酚／N-卤代丁二酰亚胺这一新的有机催化卤代体系。在该催化体系中,5 mol%叔膦即可顺利催化N-氯代丁二酰亚胺(NCS)对炔丙基醇卤代,一步合成氯代联烯。该方法具有选择性好、产率良好、操作简便、环境污染小等优点。优于已有文献报道方法。
筛选了叔膦催化剂,发现三环己基膦效果最佳。三苯基膦次之,在研究机理的过程中发现它不仅是催化剂而且是脱氧剂,常见的还原剂在该反应中并不能脱除炔醇羟基中的氧,但它们能将三苯氧膦还原成三苯基膦,从而实现催化循环。多元酚是有效的还原剂,其中1,4-苯二酚(HQ)性能最佳。
在总结实验证据基础上,提出了由炔丙醇和HQ/NCS/PPh3制备氯代联烯可能的反应机理。包括三苯基膦与N-卤代丁二酰亚胺反应生成卤代三苯基膦正离子活性中间物,它对羟基实施卤代。三苯基膦脱除羟基中的氧生成三苯氧膦。1,4-苯二酚将三苯氧膦还原成三苯基膦,完成催化循环,
筛选出了无还原剂存在时的最佳反应条件：炔丙基醇(1.0 mmol)、NXS(1.55 mmol)、PPh3(1.50 mmol)、CH2Cl2(5 mL)、-15-25℃下搅拌1h。在此条件下氯代联烯的产率最高可达88%,溴代联烯的产率最高可达86%。有还原剂存在时的最佳反应条件：炔丙基醇(1.00 mmol)、NCS(1.55 mmol)、HQ(1.5 mmol)、PPh3(5 mmol%)、CH2Cl2(5 mL),室温下搅拌24 h,氯代联烯产率最高可达85%。合成的氯代联烯和溴代联烯均未见文献报道。
Suzuki交叉偶联反应是重要的现代有机合成方法。用卤代联烯Suzuki交叉偶联反应合成含联烯结构的分子为合成药物、天然化合物探讨一个新路线的工作也具有实际意义。但卤代联烯基作为Suzuki交叉偶联反应底物之前则极少有文献报导。为此,研究了溴代联烯与芳基硼酸的Suzuki交叉偶联反应。发现二-(二苯基膦乙酸)钯是芳基溴代联烯Suzuki交叉偶联反应的有效催化剂,在室温下的催化活性很高,最高产率达93%；研究二-(二苯基膦乙酸钯)催化1-溴-1-丁基-3-(4’-溴苯基)-1,2丙二烯(3c)与苯硼酸Suzuki交叉偶联反应,发现它能高选择性地催化溴代联烯上的C-Br而不是溴苯基上的C-Br参加反应。
二-(二苯基膦乙醇)-二氯合镍也能有效地催化芳基溴代联烯Suzuki交叉偶联反应。最高产率达87%。
生成的含联烯结构的交叉偶联产物均未见文献报道。
Haloallenes which has been recognized as important fundamental organic units are often used as intermediates for the preparation of natural products and pharmaceuticals due to their high reactivity in substitution, addition, coupling and other reactions. However, the reported methods for the synthesis of haloallenes have many disadvantages such as low-yield, poor selectivity, complex manipulation and serious pollution problems. Especially, dichlorosulfoxide, concentrated hydrochloric acid and other halogenated reagents have caused severe damage to the environment. Recently, the field of enzyme catalysis and organocatalysis has been rapidly developing and attracted an increasing number of research groups around the world. Chemical transformations in this field generally possess advantages such as high efficiency, good selectivity and mild conditions, thus the synthesis of halo-allenes directed by the concept of organocatalysis is according to green chemistry concepts and would be an ideal strategy.
The reaction of propargyl alcohols with N-halogenated succinimide under the NCX/PPh3 system providing chloroallenes or bromoallenes via three stages including halogenation, oxidation and isomerization was firstly studied. It is found that PPh3 not only facilitate the step of halogenation but also act as a deoxidant. Base on this result, we proposed the triphosphine/ 1,4-hydroquinone/NXS as an novel organocatalytical system for the halogenation reaction. In this catalytical system, propargyl alcohols could be halogenated by NCS in presence of only 5 mol% of triphosphine to afford chloroallenes in one step. This method possesses a series of merits containing good selectivity, high yield, simple manipulation and limited pollution which is better than reported methods.
Triphosphines was found to be catalyst in the employed systerms, and demonstrates that Cy3P is the best catalyst, PPh3 as the second one. The research on the mechanism reveals that the triphosphine acts as catalyst and deoxidant at the same time. Generally, the oxygen atom of the propargyl alcohols can not be absorbed by reductant directly. However, the deoxidant can reduce triphenylphosphine oxide to triphenylphosphine which achieves the catalytical cycles.. Polyphenols were the effective reductant and 1,4-dihydroxybenzene was the best one.
Based on the obtained results, a proposed mechanism of the halogenation of propargyl alcohols under the HQ/NCS/PPh3 system was tentatively given. In this mechanism:hydroxyl was halogenated by Cl-PPh3 cation as the active intermediate generated by the reaction of triphenylphosphine with N-halogenated succinimide. Then the oxygen atom in hydroxyl was removed by triphenylphosphine giving triphenylphosphine oxide. At last, triphenylphosphine oxide was reduced to triphenylphosphine by 1,4-dihydroxybenzene and start a new catalytical cycle.
The optimized condition in the absence of reductant:propargyl alcohol (1.0 mmol), NXS (1.55 mmol), triphenylphosphine (1.50 mmol), CH2Cl2 (5 mL) and stirred for 1 h under-15 to 25℃. Under this condition, up to 88% and 86% yields can be obtained for chloroallene and bromoallene, respectively. In the presence of reductant:propargyl alcohol (1.0 mmol), NCS (1.55 mmol), HQ (1.5 mmol), triphenylphosphine (5 mmol%), CH2Cl2 (5 mL) and stirred for 24 h under room temperature. All the chloroallenes and bromoallenes are new compounds.
Suzuki cross-coupling reaction is one of the most important methods in modern organic synthesis. An investigation of the Suzuki cross-coupling reaction of haloallenes to synthesize natural products and pharmaceuticals containing allene structure was extraordinary significance. However, up to now only a few reports could be found in this area. Thus, suzuki cross-coupling of bromoallene and arylboric acid was studied and found that di[2-(diphenylphosphino)acetic acid] palladium was an very effective catalyst, even under room temperature the yield can reach up to 93%. It was found that C-Br on bromoallene rather than on benzene ring readily took part in Suzuki cross-coupling reaction between 1-bromo-l-butyl- (4-bromophenyl)-1,2-propadiene and aryl boric acid catalyzed by di[2-(diphenylphosphino)acetic acid] palladium.
NiCl2(Ph2PCH2CH2O)2 was also found to be a effective catalyst for the Suzuki reaction and led up to 87% yield.
All cross-coupling products of bromoallene are new compounds.
引文
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