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Polymacrocycles Derived via Ugi Multi‐Component Reactions
Macromolecular Rapid Communications ( IF 4.6 ) Pub Date : 2018-11-20 , DOI: 10.1002/marc.201800748
Patrick-Kurt Dannecker 1 , Ansgar Sehlinger 1 , Michael A. R. Meier 1
Affiliation  

The synthesis of macrocycles based on the Ugi‐4CR has been thoroughly explored by Wessjohann and coworkers, while polymerizations utilizing the Ugi‐4CR are already patented by Ugi and recently studied more in detail, developing a new trend in polymer chemistry. Here, the combination of both, that is, the synthesis of polymacrocycles, is demonstrated. As diverse functional groups can be easily introduced in a macrocycle via Ugi‐4CR, a straightforward design of polymacrocycles is achieved in a two‐step procedure. First, the Ugi‐4CR of 10‐undecenoic acid, a diamine, a diisocyanide, and an aldehyde results in diversely substituted macrocycles having two terminal double bonds. Subsequently, these macrocycles are polymerized by ADMET (acyclic diene metathesis) or thiol‐ene polymerization to generate polymacrocycles with potential application in coordination chemistry as, for example, sensors, filters, or phase‐transfer catalysts. Moreover, the setup of the literature‐known Ugi macrocyclization is simplified by systematic reaction screening.

中文翻译:

通过Ugi多组分反应衍生的多环化合物

Wessjohann及其同事已经对基于Ugi-4CR的大环化合物的合成进行了彻底的探索,而使用Ugi-4CR的聚合已获得Ugi的专利,并且最近进行了更详细的研究,从而在聚合物化学中发展了新的趋势。在此,说明了两者的组合,即多大环化合物的合成。由于可以通过Ugi‐4CR轻松地将各种官能团引入一个大环中,因此只需两步即可完成多环的简单设计。首先,10-十一碳烯酸,二胺,二异氰酸酯和醛的Ugi-4CR导致具有两个末端双键的不同取代的大环。随后,这些大环化合物通过ADMET(无环二烯复分解)或硫醇烯聚合而聚合,生成多环化合物,可在配位化学中应用,例如传感器,过滤器或相转移催化剂。此外,通过系统的反应筛选可以简化文献中已知的Ugi大环化的设置。
更新日期:2018-11-20
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