以二氧化碳为合成子形成C-N键的方法学
摘要
二氧化碳既是最主要的温室气体,同时也是地球上分布最广、储量最丰富的碳一资源。无论从资源利用还是环境保护的角度考虑,二氧化碳的固定和化学转化的研究都具有重要意义。噁唑啉酮、脲、咪唑啉酮、氨基甲酸酯等,这几类氨基甲酸衍生物均广泛应用于医药、农药、有机合成等多个重要领域,以二氧化碳为合成子构建C-N键,合成上述有机物,既可以解决二氧化碳排放过量所引起的“温室效应”问题,又可以实现二氧化碳的循环利用,实现可持续发展,是符合绿色化学观点的。
噁唑啉酮是一类重要的五元杂环化合物,在有机合成中广泛应用于有机合成中间体、手性合成助剂、生物活性化合物的合成。以二氧化碳为原料合成嗯唑啉酮,其中以二氧化碳与氮杂环丙烷的环加成反应原子经济性最高,底物适应面最广,而由烯烃作为底物,选择合适的氮源合成氮杂环丙烷,不仅大大降低了原料的成本,并且能够大规模扩展底物范围。四正丁基三溴化铵／四正丁基溴化铵双组分催化剂可以催化烯烃、氯胺-T和二氧化碳高区位选择性地一步合成5-取代-2-噁唑啉酮,其中四正丁基三溴化铵可以催化烯烃的吖啶化反应,而四正丁基溴化铵可以催化二氧化碳与氮杂环丙烷的环加成反应。对于其中两步反应——吖啶化和环加成的催化剂的选择及对反应条件的优化对于合成5-取代-2-嗯唑啉酮起着极其重要的作用。
脲衍生物是一类重要的羰基化合物,可广泛用作农业上的除草剂、杀虫剂、植物生长调节剂或医药领域中的重要中间体,并且也可作为汽油的抗氧化剂和塑料的添加剂。其中作为除草剂、杀虫剂、消毒杀菌剂、植物生长调节剂、灭鼠剂、医药或其中间体等用途的非对称取代脲类化合物现已工业化生产。脲传统的合成方法要使用光气、异氰酸酯等剧毒且高危险性的原料。由二氧化碳代替剧毒原料合成脲具有十分重要的意义。在不使用任何脱水剂的情况下,聚乙二醇1000负载氢氧化钾可以高效催化胺与二氧化碳合成对称脲,其中聚乙二醇对于碱催化这个反应有很强的促进作用,并通过核磁测试证实了反应中主客体加合物的生成。以脂肪伯胺、脂肪肿胺、脂肪邻二胺为原料合成相应的脲,均可以得到较为满意的结果。此外,催化剂可以通过简单的萃取过滤即可实现回收,重复使用5次后催化活性无明显下降。
有机氨基甲酸酯广泛应用于医药、农药,并在合成化学中作为关键中间体或保护基团。以往使用二氧化碳作为原料的合成方法往往要过量的相转移催化剂(如季铵盐)和昂贵的碱(如碳酸铯)。以聚乙二醇400作为溶剂,廉价的碳酸钾作为缚酸剂,使用胺、二氧化碳、卤代烃在温和的条件(常压室温)下能够高效且环境友好地合成氨基甲酸酯。其中聚乙二醇既作为溶剂,又可以作为相转移催化剂,从而不需要额外添加相转移催化剂。聚乙二醇的存在既可以抑制副反应——胺的烷基化,提高生成氨基甲酸酯的选择性；又可以增强碳酸钾的碱性,促进反应的进行。并且通过简单的萃取得到了产物,大大简化了分离步骤。
Carbon dioxide is the most abundant greenhouse gas and can be also regarded as a typical renewable natural resource. The development of environmentally friendly process utilizing CO2 has received much attention from the viewpoint of resources utilization and green chemistry. In this context, one of the major successes is the utilization of CO2 as the starting materials to prepare oxazolidinones, urea and carbamate via the coupling of CO2 with amines in view of green chemistry.
2-Oxazolidinones are an important class of five-membered heterocycles showing a plethora of applications as intermediates and chiral auxiliaries in organic synthesis. Cycloaddition of CO2 with nitrogen source and olefin is one of the most promising methods for synthesis of oxazolidinones. We have developed a binary catalyst system composed of n-Bu4NBr3/n-Bu4NBr for facile synthesis of 5-substituted 2-oxazolidinones with perfect regioselectivity in a single operation directly from olefins, Chloramine-T and CO2. The choice of efficient binary catalysts for two steps, i.e. aziridination and cycloaddition, and the optimization of reaction condition are keys to the one-pot synthesis of 5-substituted 2-oxazolidinones. A possible mechanism for the present one-pot synthesis of oxazolidinones was also proposed.
Urea derivatives are an important class of carbonyl compounds and useful chemical intermediates in the synthesis of Pharmaceuticals, agricultural chemicals, dyes; and they are also used as antioxidants in gasoline and additives in plastics. Therefore, the synthesis of ureas starting from CO2 has drawn much attention because CO2 is a renewable, abundant, cheap, and non-toxic source of functional carbon unit. We have developed polyethylene glycol-supported potassium hydroxide (KOH/PEG1000) as a recyclable catalyst for facile synthesis of urea derivatives from amines and CO2 without utilization of additional dehydrating agents. Primary aliphatic amines, secondary aliphatic amines and diamines can be converted into the corresponding urea derivatives in moderate yields. Furthermore, the catalyst can be recovered after a simple separation procedure, and reused over 5 times with retention of high activity.
Organic carbamates hold extensive applications in pharmaceutical industry, agriculture and have been widely used as key intermediates or protecting groups in synthetic chemistry. We have developed an efficient and environmentally benign method for the synthesis of organic carbamates. Amines, CO2 and alkyl halides underwent a three-component reaction with the aid of K2CO3 and polyethylene glycol (PEG400, MW=400), affording the organic carbamates under ambient conditions. PEG could presumably act as a solvent, phase transfer catalyst (PTC). Notably, the presence of PEG could also depress the alkylation of both the amine and the carbamate, thus resulting in enhanced selectivity toward the target carbamate.
噁唑啉酮是一类重要的五元杂环化合物,在有机合成中广泛应用于有机合成中间体、手性合成助剂、生物活性化合物的合成。以二氧化碳为原料合成嗯唑啉酮,其中以二氧化碳与氮杂环丙烷的环加成反应原子经济性最高,底物适应面最广,而由烯烃作为底物,选择合适的氮源合成氮杂环丙烷,不仅大大降低了原料的成本,并且能够大规模扩展底物范围。四正丁基三溴化铵／四正丁基溴化铵双组分催化剂可以催化烯烃、氯胺-T和二氧化碳高区位选择性地一步合成5-取代-2-噁唑啉酮,其中四正丁基三溴化铵可以催化烯烃的吖啶化反应,而四正丁基溴化铵可以催化二氧化碳与氮杂环丙烷的环加成反应。对于其中两步反应——吖啶化和环加成的催化剂的选择及对反应条件的优化对于合成5-取代-2-嗯唑啉酮起着极其重要的作用。
脲衍生物是一类重要的羰基化合物,可广泛用作农业上的除草剂、杀虫剂、植物生长调节剂或医药领域中的重要中间体,并且也可作为汽油的抗氧化剂和塑料的添加剂。其中作为除草剂、杀虫剂、消毒杀菌剂、植物生长调节剂、灭鼠剂、医药或其中间体等用途的非对称取代脲类化合物现已工业化生产。脲传统的合成方法要使用光气、异氰酸酯等剧毒且高危险性的原料。由二氧化碳代替剧毒原料合成脲具有十分重要的意义。在不使用任何脱水剂的情况下,聚乙二醇1000负载氢氧化钾可以高效催化胺与二氧化碳合成对称脲,其中聚乙二醇对于碱催化这个反应有很强的促进作用,并通过核磁测试证实了反应中主客体加合物的生成。以脂肪伯胺、脂肪肿胺、脂肪邻二胺为原料合成相应的脲,均可以得到较为满意的结果。此外,催化剂可以通过简单的萃取过滤即可实现回收,重复使用5次后催化活性无明显下降。
有机氨基甲酸酯广泛应用于医药、农药,并在合成化学中作为关键中间体或保护基团。以往使用二氧化碳作为原料的合成方法往往要过量的相转移催化剂(如季铵盐)和昂贵的碱(如碳酸铯)。以聚乙二醇400作为溶剂,廉价的碳酸钾作为缚酸剂,使用胺、二氧化碳、卤代烃在温和的条件(常压室温)下能够高效且环境友好地合成氨基甲酸酯。其中聚乙二醇既作为溶剂,又可以作为相转移催化剂,从而不需要额外添加相转移催化剂。聚乙二醇的存在既可以抑制副反应——胺的烷基化,提高生成氨基甲酸酯的选择性；又可以增强碳酸钾的碱性,促进反应的进行。并且通过简单的萃取得到了产物,大大简化了分离步骤。
Carbon dioxide is the most abundant greenhouse gas and can be also regarded as a typical renewable natural resource. The development of environmentally friendly process utilizing CO2 has received much attention from the viewpoint of resources utilization and green chemistry. In this context, one of the major successes is the utilization of CO2 as the starting materials to prepare oxazolidinones, urea and carbamate via the coupling of CO2 with amines in view of green chemistry.
2-Oxazolidinones are an important class of five-membered heterocycles showing a plethora of applications as intermediates and chiral auxiliaries in organic synthesis. Cycloaddition of CO2 with nitrogen source and olefin is one of the most promising methods for synthesis of oxazolidinones. We have developed a binary catalyst system composed of n-Bu4NBr3/n-Bu4NBr for facile synthesis of 5-substituted 2-oxazolidinones with perfect regioselectivity in a single operation directly from olefins, Chloramine-T and CO2. The choice of efficient binary catalysts for two steps, i.e. aziridination and cycloaddition, and the optimization of reaction condition are keys to the one-pot synthesis of 5-substituted 2-oxazolidinones. A possible mechanism for the present one-pot synthesis of oxazolidinones was also proposed.
Urea derivatives are an important class of carbonyl compounds and useful chemical intermediates in the synthesis of Pharmaceuticals, agricultural chemicals, dyes; and they are also used as antioxidants in gasoline and additives in plastics. Therefore, the synthesis of ureas starting from CO2 has drawn much attention because CO2 is a renewable, abundant, cheap, and non-toxic source of functional carbon unit. We have developed polyethylene glycol-supported potassium hydroxide (KOH/PEG1000) as a recyclable catalyst for facile synthesis of urea derivatives from amines and CO2 without utilization of additional dehydrating agents. Primary aliphatic amines, secondary aliphatic amines and diamines can be converted into the corresponding urea derivatives in moderate yields. Furthermore, the catalyst can be recovered after a simple separation procedure, and reused over 5 times with retention of high activity.
Organic carbamates hold extensive applications in pharmaceutical industry, agriculture and have been widely used as key intermediates or protecting groups in synthetic chemistry. We have developed an efficient and environmentally benign method for the synthesis of organic carbamates. Amines, CO2 and alkyl halides underwent a three-component reaction with the aid of K2CO3 and polyethylene glycol (PEG400, MW=400), affording the organic carbamates under ambient conditions. PEG could presumably act as a solvent, phase transfer catalyst (PTC). Notably, the presence of PEG could also depress the alkylation of both the amine and the carbamate, thus resulting in enhanced selectivity toward the target carbamate.
引文
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