Synthesis of Pyrimidine-Modified NHC Ruthenium-Alkylidene Catalysts and Their Application in RCM, CM, EM and ROMP Reactions

• Published in: European journal of organic chemistry 2012-12, Vol.2012 (34), p.6777-6784
• Main Authors: Wu, Guang-Long, Cao, Sheng-Li, Chen, Jian, Chen, Zili
• Format: Article
• Language: English
• Subjects: Catalysis; Catalysts: preparations and properties; Catalytic reactions; Chemistry; Exact sciences and technology; General and physical chemistry; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Homogeneous catalysis; Metathesis; Nitrogen heterocycles; Organic chemistry; Preparations and properties; Ruthenium; Synthetic methods; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201200989

A new type of N‐heterocyclic carbene bearing ruthenium olefin metathesis catalyst was prepared through the incorporation of a chelated pyrimidinyl methylene subunit, in which electron‐rich substituents were attached to stabilize the ruthenium complexes. These catalysts were successfully used in various types of olefin metathesis reactions, including ring‐closing metathesis (RCM), cross‐metathesis (CM), enyne metathesis (EM), and ring‐opening metathesis polymerization (ROMP) reactions. The results therein showed that the presence of an electron‐deficient pyrimidine structure greatly enhanced the new NHC ruthenium complexes' catalytic activities. New N‐heterocyclic carbene bearing ruthenium olefin metathesis catalysts were synthesized and applied in various types of olefin metathesis reactions, including ring‐closing metathesis, cross‐metathesis, enyne metathesis, and ring‐opening metathesis polymerization reactions.