Cu（OTf）_2催化的以卤代烃为原料的Ritter反应
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摘要
酰胺化合物的重要作用是不言而喻的。因酰胺键不仅存在于生命体的重要组成部分蛋白质中；且存在于日常生活用品的组成成份纤维中；同时在农业方面也扮演重要的角色，一些除草剂和除虫剂是酰胺类化合物；也是药物化学研究的重点，是一些药物分子的重要结构。
鉴于此，构筑酰胺键也成为化学家研究的重点。现在，许多课题组已致力于酰胺键构筑的研究，并对酰胺键形成的反应进行了报道。但利用腈类化合物作为酰胺化试剂，仍然是一个挑战。那么基于腈类化合物作为起始原料的Ritter反应，也就成为了研究的重点。文献中关于Ritter反应的报道，主要集中在对其催化剂的改进，而且大部分是对腈和醇的Ritter反应催化剂的改进。
基于此，我们选择金属化合物—Cu(OTf)_2作为催化剂，催化腈类化合物和文献中很少报道的卤代烃的Ritter反应。此方案在方法学上具有一定的创新性。在此系统下，我们合成了近20个酰胺类化合物。
所有化合物的结构均经1H-NMR、13C-NMR确认，部分化合物经HRMS确认。
本论文首次采用Cu(OTf)_2催化Ritter反应，同时是对文献中很少报道的卤代烃进行酰胺化。与文献报道的方法相比，该方法操作简单，产率高，为酰胺类化合物的合成提供了一种新方法。
The amide functionality-the unique structure-is an important building block of proteins, manynatural products and synthetic materials which has fascinated organic chemists for a long time.
Despite numerous approaches for the formation of amides reported in the literature, the use ofnitriles as starting materials remains emerging area. A representative and important strategy within this fieldrelies on the Ritter reaction, which is based on the reaction of aliphatic-or aromatic-nitriles andcarbocations in the presence of strong acid. Considerable effort has been devoted to the development ofcatalysts (such as Lewis acids etc.) in the past decades.
While, we are surprised to find that, to the best of our knowledge, halohydrocarbons have rarelybeen the subject of the Ritter reaction. Thus, new system utilizing metal catalyst with a new startingmaterial would be highly desirable. Herein, an efficient and general methodology was reported for thesynthesis of amides via the reaction of nitriles and halohydrocarbons employing Cu(OTf)_2as catalyst inwater and the target products were achieved in satisfactory yields.
The structures of title compounds were confirmed by1H-NMR,13C-NMR, some of them wereconfirmed by HRMS.
By this procedure, Cu(OTf)_2turned out to be economically efficient catalyst for the Ritterreaction, and a wide range of halohydrocarbons were employed to couple with nitriles instead of alcoholsor alkenes, which expanded the scope of the Ritter reaction by using halohydrocarbons as a startingmaterial.
鉴于此，构筑酰胺键也成为化学家研究的重点。现在，许多课题组已致力于酰胺键构筑的研究，并对酰胺键形成的反应进行了报道。但利用腈类化合物作为酰胺化试剂，仍然是一个挑战。那么基于腈类化合物作为起始原料的Ritter反应，也就成为了研究的重点。文献中关于Ritter反应的报道，主要集中在对其催化剂的改进，而且大部分是对腈和醇的Ritter反应催化剂的改进。
基于此，我们选择金属化合物—Cu(OTf)_2作为催化剂，催化腈类化合物和文献中很少报道的卤代烃的Ritter反应。此方案在方法学上具有一定的创新性。在此系统下，我们合成了近20个酰胺类化合物。
所有化合物的结构均经1H-NMR、13C-NMR确认，部分化合物经HRMS确认。
本论文首次采用Cu(OTf)_2催化Ritter反应，同时是对文献中很少报道的卤代烃进行酰胺化。与文献报道的方法相比，该方法操作简单，产率高，为酰胺类化合物的合成提供了一种新方法。
The amide functionality-the unique structure-is an important building block of proteins, manynatural products and synthetic materials which has fascinated organic chemists for a long time.
Despite numerous approaches for the formation of amides reported in the literature, the use ofnitriles as starting materials remains emerging area. A representative and important strategy within this fieldrelies on the Ritter reaction, which is based on the reaction of aliphatic-or aromatic-nitriles andcarbocations in the presence of strong acid. Considerable effort has been devoted to the development ofcatalysts (such as Lewis acids etc.) in the past decades.
While, we are surprised to find that, to the best of our knowledge, halohydrocarbons have rarelybeen the subject of the Ritter reaction. Thus, new system utilizing metal catalyst with a new startingmaterial would be highly desirable. Herein, an efficient and general methodology was reported for thesynthesis of amides via the reaction of nitriles and halohydrocarbons employing Cu(OTf)_2as catalyst inwater and the target products were achieved in satisfactory yields.
The structures of title compounds were confirmed by1H-NMR,13C-NMR, some of them wereconfirmed by HRMS.
By this procedure, Cu(OTf)_2turned out to be economically efficient catalyst for the Ritterreaction, and a wide range of halohydrocarbons were employed to couple with nitriles instead of alcoholsor alkenes, which expanded the scope of the Ritter reaction by using halohydrocarbons as a startingmaterial.
引文
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